Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 182 _publ_contact_author_name 'Prof Robin D Rogers' _publ_contact_author_address ; Center for Green Manufacturing and Department of Chemistry The University of Alabama Tuscaloosa, AL 35487 USA ; _publ_contact_author_email rdrogers@bama.ua.edu loop_ _publ_author_name _publ_author_address 'John D. Holbrey' ; Center for Green Manufacturing The University of Alabama Tuscaloosa, AL 35487 USA ; 'W. Matthew Reichert' ; Center for Green Manufacturing and Department of Chemistry The University of Alabama Tuscaloosa, AL 35487 USA ; 'Mark Nieuwenhuyzen' ; Department of Chemistry Queen's University of Belfast Belfast BT9 5AG Northern Ireland, UK ; 'Suzanne Johnson' ; QUILL Queen's University of Belfast Belfast BT9 5AG Northern Ireland, UK ; 'Kenneth R. Seddon' ; QUILL and Department of Chemistry Queen's University of Belfast Belfast BT9 5AG Northern Ireland, UK ; 'Robin D., Rogers' ; Center for Green Manufacturing and Department of Chemistry The University of Alabama Tuscaloosa, AL 35487 USA ; _publ_requested_journal 'Chemical Communications' _publ_section_title ; Crystal polymorphism in 1-butyl-3-methlimidazolium halides: supporting ionic liquid formation by inhibition of crystallisation ; data_bmimclor _database_code_CSD 211518 _audit_creation_method SHELXL-97 _chemical_name_systematic '1-butyl-3-methylimidazolium chloride' _chemical_name_common '1-butyl-3-methylimidazolium chloride' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H15 Cl N2' _chemical_formula_weight 174.67 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pna21 _symmetry_Int_Tables_number 33 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 10.113(2) _cell_length_b 11.411(2) _cell_length_c 8.3285(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 961.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 986 _cell_measurement_theta_min 0.55 _cell_measurement_theta_max 0.97 _exptl_crystal_description fragment _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.207 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.341 _exptl_absorpt_correction_type sphere _exptl_absorpt_correction_T_min 0.78 _exptl_absorpt_correction_T_max 0.97 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_probe x-ray _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3952 _diffrn_reflns_av_R_equivalents 0.0507 _diffrn_reflns_av_sigmaI/netI 0.0384 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 23.24 _reflns_number_total 1351 _reflns_number_gt 1287 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0696P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00 _refine_ls_number_reflns 1351 _refine_ls_number_parameters 160 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0421 _refine_ls_R_factor_gt 0.0405 _refine_ls_wR_factor_ref 0.0919 _refine_ls_wR_factor_gt 0.0907 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.05908(5) 0.57457(5) 0.41094(10) 0.0326(2) Uani 1 1 d . . . N1 N 0.2667(2) 0.2641(2) 0.2825(3) 0.0248(5) Uani 1 1 d . . . N3 N 0.2468(2) 0.2464(2) 0.5385(3) 0.0270(6) Uani 1 1 d . . . C2 C 0.2071(2) 0.3078(2) 0.4105(4) 0.0268(5) Uani 1 1 d . . . H2A H 0.152(2) 0.365(2) 0.418(4) 0.019(5) Uiso 1 1 d . . . C4 C 0.3361(3) 0.1610(2) 0.4881(3) 0.0283(7) Uani 1 1 d . . . H4A H 0.379(3) 0.115(3) 0.558(4) 0.023(8) Uiso 1 1 d . . . C5 C 0.3475(3) 0.1738(3) 0.3281(4) 0.0270(7) Uani 1 1 d . . . H5A H 0.393(4) 0.134(3) 0.257(5) 0.035(9) Uiso 1 1 d . . . C6 C 0.2010(4) 0.2664(4) 0.7038(4) 0.0442(8) Uani 1 1 d . . . H6A H 0.142(5) 0.217(4) 0.733(6) 0.070(13) Uiso 1 1 d . . . H6B H 0.147(4) 0.335(4) 0.703(5) 0.056(12) Uiso 1 1 d . . . H6C H 0.247(6) 0.242(4) 0.785(7) 0.075(15) Uiso 1 1 d . . . C7 C 0.2548(3) 0.3129(3) 0.1178(4) 0.0310(6) Uani 1 1 d . . . H7A H 0.281(3) 0.250(3) 0.059(3) 0.021(8) Uiso 1 1 d . . . H7B H 0.177(5) 0.335(4) 0.104(6) 0.073(15) Uiso 1 1 d . . . C8 C 0.3420(3) 0.4196(2) 0.0958(4) 0.0329(7) Uani 1 1 d . . . H8B H 0.322(3) 0.478(2) 0.188(3) 0.024(6) Uiso 1 1 d . . . H8A H 0.317(3) 0.454(2) -0.010(4) 0.028(7) Uiso 1 1 d . . . C9 C 0.4905(3) 0.3925(3) 0.0989(4) 0.0378(7) Uani 1 1 d . . . H9B H 0.515(4) 0.351(3) 0.204(4) 0.050(9) Uiso 1 1 d . . . H9A H 0.509(4) 0.332(3) 0.010(4) 0.058(10) Uiso 1 1 d . . . C10 C 0.5743(4) 0.5009(4) 0.0762(5) 0.0530(9) Uani 1 1 d . . . H10B H 0.559(3) 0.561(4) 0.167(6) 0.053(12) Uiso 1 1 d . . . H10C H 0.662(5) 0.466(4) 0.051(5) 0.067(11) Uiso 1 1 d . . . H10A H 0.546(4) 0.539(4) -0.026(5) 0.071(13) 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 Cl1 0.0312(4) 0.0296(4) 0.0370(4) -0.0006(3) -0.0025(3) 0.0007(2) N1 0.0211(11) 0.0277(12) 0.0255(13) -0.0007(10) 0.0000(10) -0.0018(9) N3 0.0210(14) 0.0310(14) 0.0289(14) -0.0018(10) 0.0041(9) -0.0006(9) C2 0.0213(12) 0.0261(12) 0.0329(13) -0.0025(14) -0.0029(14) 0.0021(10) C4 0.0237(16) 0.0270(15) 0.0343(19) 0.0033(12) 0.0007(12) -0.0014(12) C5 0.0220(14) 0.0261(15) 0.0329(18) -0.0030(11) 0.0048(12) -0.0019(11) C6 0.047(2) 0.058(2) 0.0278(18) -0.0002(16) 0.0099(16) 0.004(2) C7 0.0257(15) 0.0396(17) 0.0278(14) -0.0004(13) -0.0065(13) 0.0022(12) C8 0.0326(17) 0.0346(16) 0.0315(16) 0.0069(12) -0.0016(13) 0.0030(11) C9 0.0315(16) 0.0387(16) 0.0432(17) 0.0040(16) 0.0043(15) 0.0022(14) C10 0.0382(19) 0.051(2) 0.070(3) 0.015(2) 0.0063(17) -0.0036(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.322(4) . ? N1 C5 1.369(4) . ? N1 C7 1.485(4) . ? N3 C2 1.337(4) . ? N3 C4 1.394(4) . ? N3 C6 1.470(4) . ? C4 C5 1.345(4) . ? C7 C8 1.515(4) . ? C8 C9 1.534(4) . ? C9 C10 1.511(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C5 109.4(2) . . ? C2 N1 C7 124.5(2) . . ? C5 N1 C7 125.9(3) . . ? C2 N3 C4 108.7(2) . . ? C2 N3 C6 124.8(2) . . ? C4 N3 C6 126.5(3) . . ? N1 C2 N3 108.0(2) . . ? C5 C4 N3 106.1(3) . . ? C4 C5 N1 107.8(3) . . ? N1 C7 C8 111.5(2) . . ? C7 C8 C9 113.9(2) . . ? C10 C9 C8 112.5(3) . . ? 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 N1 C7 C8 C9 68.0(3) . . . . ? C2 N1 C7 C8 78.9(3) . . . . ? C7 C8 C9 C10 179.9(3) . . . . ? C5 N1 C7 C8 -95.9(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C2 H2A Cl1 0.87(2) 2.56(2) 3.392(3) 160(2) . C7 H7A Cl1 0.91(3) 2.85(3) 3.730(4) 162(2) 4_544 C6 H6B Cl1 0.96(4) 2.90(4) 3.631(4) 134(3) 2_565 C6 H6C Cl1 0.87(6) 2.93(6) 3.696(4) 148(4) 4_545 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 23.24 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.240 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.045 data_bmimcl3 _database_code_CSD 211519 _audit_creation_method SHELXL-97 _chemical_name_systematic '1-butyl-3-methylimidazolium chloride' _chemical_name_common '1-butyl-3-methylimidazolium chloride' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H15 Cl N2' _chemical_formula_weight 174.67 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_Int_Tables_number 14 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 9.943(9) _cell_length_b 11.481(10) _cell_length_c 9.658(9) _cell_angle_alpha 90.00 _cell_angle_beta 118.740(15) _cell_angle_gamma 90.00 _cell_volume 966.6(15) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 876 _cell_measurement_theta_min 0.69 _cell_measurement_theta_max 0.97 _exptl_crystal_description fragment _exptl_crystal_colour colorless _exptl_crystal_size_max 0.8 _exptl_crystal_size_mid 0.6 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.200 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.339 _exptl_absorpt_correction_type sphere _exptl_absorpt_correction_T_min 0.78 _exptl_absorpt_correction_T_max 0.97 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_probe x-ray _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4181 _diffrn_reflns_av_R_equivalents 0.0250 _diffrn_reflns_av_sigmaI/netI 0.0178 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 23.27 _reflns_number_total 1385 _reflns_number_gt 1257 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0515P)^2^+0.1208P] 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 1385 _refine_ls_number_parameters 160 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0292 _refine_ls_R_factor_gt 0.0264 _refine_ls_wR_factor_ref 0.0746 _refine_ls_wR_factor_gt 0.0729 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _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 Cl1 Cl 0.25933(4) 0.93049(3) 0.09179(4) 0.03163(18) Uani 1 1 d . . . N1 N 1.07017(14) 1.23886(10) 0.76809(13) 0.0267(3) Uani 1 1 d . . . N3 N 1.31620(13) 1.23743(10) 0.91922(13) 0.0283(3) Uani 1 1 d . . . C2 C 1.18618(17) 1.18274(14) 0.88524(16) 0.0279(4) Uani 1 1 d . . . H2A H 1.1768(17) 1.1172(16) 0.9290(18) 0.030(4) Uiso 1 1 d . . . C4 C 1.28205(18) 1.33185(13) 0.81932(17) 0.0304(4) Uani 1 1 d . . . H4A H 1.3591(18) 1.3821(14) 0.8244(17) 0.028(4) Uiso 1 1 d . . . C5 C 1.12898(18) 1.33249(13) 0.72513(18) 0.0304(4) Uani 1 1 d . . . H5A H 1.0624(18) 1.3797(15) 0.643(2) 0.033(4) Uiso 1 1 d . . . C6 C 1.4689(2) 1.20101(17) 1.0416(2) 0.0378(4) Uani 1 1 d . . . H6A H 1.453(2) 1.1316(18) 1.093(2) 0.049(5) Uiso 1 1 d . . . H6B H 1.516(2) 1.2630(17) 1.115(2) 0.048(5) Uiso 1 1 d . . . H6C H 1.532(2) 1.1817(15) 0.997(2) 0.043(5) Uiso 1 1 d . . . C7 C 0.90937(17) 1.19944(14) 0.68494(18) 0.0297(4) Uani 1 1 d . . . H7A H 0.8495(19) 1.2666(16) 0.642(2) 0.034(4) Uiso 1 1 d . . . H7B H 0.8856(16) 1.1656(13) 0.7583(19) 0.028(4) Uiso 1 1 d . . . C8 C 0.88476(17) 1.11324(15) 0.55573(18) 0.0323(4) Uani 1 1 d . . . H8A H 0.9231(18) 1.1478(15) 0.490(2) 0.037(4) Uiso 1 1 d . . . H8B H 0.9440(19) 1.0437(16) 0.6043(19) 0.038(4) Uiso 1 1 d . . . C9 C 0.71679(18) 1.07988(14) 0.45557(19) 0.0339(4) Uani 1 1 d . . . H9A H 0.6602(18) 1.1484(16) 0.4042(19) 0.034(4) Uiso 1 1 d . . . H9B H 0.6746(19) 1.0525(14) 0.529(2) 0.038(4) Uiso 1 1 d . . . C10 C 0.6953(2) 0.98570(16) 0.3360(2) 0.0417(4) Uani 1 1 d . . . H10A H 0.591(3) 0.9656(19) 0.280(2) 0.063(6) Uiso 1 1 d . . . H10B H 0.754(2) 0.9150(18) 0.390(2) 0.052(5) Uiso 1 1 d . . . H10C H 0.737(2) 1.0162(17) 0.263(2) 0.049(5) 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 Cl1 0.0385(3) 0.0238(3) 0.0348(3) -0.00173(14) 0.0194(2) -0.00245(15) N1 0.0315(7) 0.0236(6) 0.0257(6) 0.0023(5) 0.0142(6) 0.0005(5) N3 0.0318(7) 0.0263(7) 0.0257(6) 0.0002(5) 0.0131(6) -0.0004(5) C2 0.0366(9) 0.0230(8) 0.0253(7) 0.0020(6) 0.0159(7) -0.0005(7) C4 0.0372(9) 0.0246(8) 0.0317(8) 0.0002(6) 0.0184(7) -0.0039(7) C5 0.0408(10) 0.0233(8) 0.0283(8) 0.0037(7) 0.0177(7) 0.0021(7) C6 0.0324(9) 0.0405(10) 0.0337(9) 0.0024(8) 0.0105(8) 0.0007(8) C7 0.0299(9) 0.0287(9) 0.0311(8) 0.0038(7) 0.0151(7) 0.0005(7) C8 0.0304(8) 0.0322(9) 0.0327(8) 0.0019(7) 0.0141(7) 0.0015(7) C9 0.0303(9) 0.0315(10) 0.0357(9) 0.0039(7) 0.0125(7) 0.0027(7) C10 0.0354(10) 0.0376(10) 0.0419(10) -0.0031(8) 0.0104(8) -0.0007(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 N1 C2 1.331(2) . ? N1 C5 1.379(2) . ? N1 C7 1.473(2) . ? N3 C2 1.329(2) . ? N3 C4 1.381(2) . ? N3 C6 1.467(2) . ? C4 C5 1.346(3) . ? C7 C8 1.517(2) . ? C8 C9 1.523(3) . ? C9 C10 1.520(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C5 108.27(14) . . ? C2 N1 C7 125.77(13) . . ? C5 N1 C7 125.53(13) . . ? C2 N3 C4 108.38(13) . . ? C2 N3 C6 124.86(14) . . ? C4 N3 C6 126.76(13) . . ? N3 C2 N1 108.90(15) . . ? C5 C4 N3 107.14(14) . . ? C4 C5 N1 107.31(14) . . ? N1 C7 C8 110.62(13) . . ? C7 C8 C9 112.36(14) . . ? C10 C9 C8 111.85(14) . . ? 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 N1 C7 C8 C9 -174.02(13) . . . . ? C2 N1 C7 C8 -83.10(19) . . . . ? C7 C8 C9 C10 -175.00(14) . . . . ? C5 N1 C7 C8 88.52(18) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C2 H2A Cl1 0.890(19) 2.549(19) 3.391(3) 158.1(13) 1_656 C4 H4A Cl1 0.941(17) 2.918(15) 3.442(3) 116.4(10) 4_686 C5 H5A Cl1 0.928(17) 2.955(17) 3.765(3) 146.7(12) 2_655 C6 H6C Cl1 0.942(19) 2.90(2) 3.819(3) 165.6(14) 3_776 C7 H7A Cl1 0.940(18) 2.731(19) 3.561(3) 147.7(13) 2_655 C7 H7B Cl1 0.933(17) 2.720(17) 3.629(3) 165.0(12) 3_676 C10 H10A Cl1 0.94(2) 2.93(2) 3.863(4) 173.5(17) . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 23.27 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.162 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.036 _ccdc_chemical_compound_source_recrystallisation none data_bmimbr _database_code_CSD 211520 _audit_creation_method SHELXL-97 _chemical_name_systematic '1-butyl-3-methylimidazolium bromide' _chemical_name_common '1-butyl-3-methylimidazolium bromide' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H15 Br N2' _chemical_formula_weight 219.13 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pna21 _symmetry_Int_Tables_number 33 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 10.0649(4) _cell_length_b 11.8628(5) _cell_length_c 8.4306(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1006.60(7) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 964 _cell_measurement_theta_min 0.52 _cell_measurement_theta_max 0.97 _exptl_crystal_description Fragment _exptl_crystal_colour Colorless _exptl_crystal_size_max 1.1 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.446 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 4.030 _exptl_absorpt_correction_type sphere _exptl_absorpt_correction_T_min 0.78 _exptl_absorpt_correction_T_max 0.97 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_probe x-ray _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6023 _diffrn_reflns_av_R_equivalents 0.1051 _diffrn_reflns_av_sigmaI/netI 0.0758 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 27.87 _reflns_number_total 2298 _reflns_number_gt 2018 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0639P)^2^+2.0282P] 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 0.005(2) _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 0.00 _refine_ls_number_reflns 2298 _refine_ls_number_parameters 161 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0674 _refine_ls_R_factor_gt 0.0552 _refine_ls_wR_factor_ref 0.1286 _refine_ls_wR_factor_gt 0.1216 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 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 Br Br 0.05720(4) 0.57487(4) 0.41010(19) 0.02586(19) Uani 1 1 d . . . N1 N 0.2698(6) 0.2652(6) 0.2830(7) 0.0224(12) Uani 1 1 d . . . N3 N 0.2467(6) 0.2455(6) 0.5353(7) 0.0228(14) Uani 1 1 d . . . C2 C 0.2090(4) 0.3081(4) 0.4117(13) 0.0250(9) Uani 1 1 d . . . H2A H 0.150(6) 0.384(5) 0.415(14) 0.031(14) Uiso 1 1 d . . . C4 C 0.3329(7) 0.1609(7) 0.4848(9) 0.0251(17) Uani 1 1 d . . . H4A H 0.371(8) 0.104(7) 0.555(8) 0.016(18) Uiso 1 1 d . . . C5 C 0.3458(7) 0.1762(7) 0.3264(8) 0.0215(15) Uani 1 1 d . . . H5A H 0.385(8) 0.134(7) 0.256(8) 0.017(19) Uiso 1 1 d . . . C6 C 0.2004(9) 0.2671(9) 0.6983(8) 0.0432(19) Uani 1 1 d . . . H6A H 0.148(11) 0.217(10) 0.726(12) 0.06(3) Uiso 1 1 d . . . H6B H 0.136(11) 0.350(10) 0.676(11) 0.06(3) Uiso 1 1 d . . . H6C H 0.275(8) 0.294(7) 0.753(9) 0.019(19) Uiso 1 1 d . . . C7 C 0.2564(7) 0.3127(6) 0.1233(8) 0.0301(14) Uani 1 1 d . . . H7A H 0.272(8) 0.242(7) 0.045(8) 0.022(17) Uiso 1 1 d . . . H7B H 0.176(7) 0.338(7) 0.102(8) 0.022(17) Uiso 1 1 d . . . C8 C 0.3411(7) 0.4174(6) 0.1024(7) 0.0310(13) Uani 1 1 d . . . H8A H 0.311(6) 0.476(6) 0.178(8) 0.016(14) Uiso 1 1 d . . . H8B H 0.329(9) 0.460(8) 0.006(9) 0.04(2) Uiso 1 1 d . . . C9 C 0.4892(8) 0.3952(7) 0.1091(9) 0.0394(15) Uani 1 1 d . . . H9A H 0.500(9) 0.338(7) 0.015(9) 0.04(2) Uiso 1 1 d . . . H9B H 0.517(9) 0.367(8) 0.209(10) 0.04(2) Uiso 1 1 d . . . C10 C 0.5714(11) 0.5031(10) 0.0925(16) 0.061(3) Uani 1 1 d . . . H10A H 0.545(12) 0.530(13) 0.005(14) 0.07(4) Uiso 1 1 d . . . H10B H 0.552(12) 0.561(10) 0.158(16) 0.07(4) Uiso 1 1 d . . . H10C H 0.656(13) 0.487(10) 0.064(13) 0.07(3) 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 Br 0.0255(3) 0.0257(3) 0.0264(2) -0.0012(4) -0.0008(4) 0.00145(18) N1 0.020(2) 0.026(3) 0.022(2) 0.003(2) 0.0001(19) -0.001(2) N3 0.018(3) 0.027(3) 0.023(3) 0.000(2) 0.0048(19) 0.003(2) C2 0.0194(19) 0.029(2) 0.0268(19) -0.008(4) -0.003(4) 0.0024(18) C4 0.023(3) 0.020(3) 0.032(4) -0.005(3) 0.000(3) 0.003(3) C5 0.020(3) 0.025(4) 0.019(3) -0.002(2) 0.002(2) 0.001(3) C6 0.040(4) 0.065(6) 0.025(3) -0.002(3) 0.017(3) 0.010(5) C7 0.024(3) 0.045(4) 0.021(3) 0.003(3) -0.006(3) 0.005(3) C8 0.031(3) 0.032(3) 0.030(3) 0.010(2) -0.001(2) 0.002(3) C9 0.032(3) 0.041(4) 0.046(4) 0.007(3) 0.009(3) 0.006(3) C10 0.042(5) 0.052(6) 0.090(8) 0.021(6) 0.011(5) -0.007(4) _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 C2 1.346(11) . ? N1 C5 1.354(11) . ? N1 C7 1.466(8) . ? N3 C2 1.335(12) . ? N3 C4 1.393(10) . ? N3 C6 1.473(8) . ? C4 C5 1.354(7) . ? C7 C8 1.517(10) . ? C8 C9 1.515(9) . ? C9 C10 1.530(13) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C5 109.5(6) . . ? C2 N1 C7 123.6(6) . . ? C5 N1 C7 126.9(6) . . ? C2 N3 C4 109.8(6) . . ? C2 N3 C6 122.8(6) . . ? C4 N3 C6 127.4(7) . . ? N3 C2 N1 106.8(4) . . ? C5 C4 N3 105.4(8) . . ? C4 C5 N1 108.4(8) . . ? N1 C7 C8 111.7(5) . . ? C9 C8 C7 114.0(6) . . ? C8 C9 C10 112.5(7) . . ? 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 N1 C7 C8 C9 66.2(8) . . . . ? C2 N1 C7 C8 77.7(8) . . . . ? C7 C8 C9 C10 -178.3(8) . . . . ? C5 N1 C7 C8 -100.1(9) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C2 H2A Br 1.08(6) 2.45(6) 3.514(5) 169(5) . C4 H4A Br 0.98(8) 3.09(8) 3.649(8) 118(5) 3 C5 H5A Br 0.87(8) 3.05(7) 3.836(7) 151(6) 4_544 C6 H6B Br 1.19(12) 2.91(11) 3.664(7) 121(6) 2_565 C7 H7A Br 1.08(7) 2.86(7) 3.836(7) 150(6) 4_544 C7 H7B Br 0.88(8) 3.03(8) 3.869(6) 160(6) 2_564 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 1.222 _refine_diff_density_min -1.023 _refine_diff_density_rms 0.141 _ccdc_chemical_compound_source_recrystallisation none