# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_IL
_database_code_depnum_ccdc_archive 'CCDC 1412428'
_audit_update_record             
;
2015-07-13 deposited with the CCDC.
2015-09-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        '1-butyl-2,3-methylimidazolium chloride'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H17 N2, Cl'
_chemical_formula_sum            'C9 H17 Cl N2'
_chemical_formula_weight         188.70

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   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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                   8.31680(10)
_cell_length_b                   11.6769(2)
_cell_length_c                   10.7135(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.6960(10)
_cell_angle_gamma                90.00
_cell_volume                     1040.36(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3646
_cell_measurement_theta_min      3
_cell_measurement_theta_max      30

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408
_exptl_absorpt_coefficient_mu    0.320
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.924
_exptl_absorpt_correction_T_max  0.938
_exptl_absorpt_process_details   'APEX2 (Bruker, 2005)'

_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  'Bruker SMART APEX2 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            87263
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_sigmaI/netI    0.0198
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.58
_diffrn_reflns_theta_max         50.00
_reflns_number_total             10763
_reflns_number_gt                6746
_reflns_threshold_expression     I>2/s(I)

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'APEX2 (Bruker, 2005)'
_computing_structure_solution    'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_computing_structure_refinement  'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_computing_molecular_graphics    'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_computing_publication_material  'SHELXTL ver. 5.1 (Sheldrick, 1998b)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0470P)²+0.1000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         10763
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0360
_refine_ls_wR_factor_ref         0.1188
_refine_ls_wR_factor_gt          0.0919
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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 0.065599(19) 0.208766(13) 0.268871(16) 0.03331(4) Uani 1 1 d . . .
N1 N 0.60915(5) 0.04395(4) 0.35301(4) 0.02474(7) Uani 1 1 d . . .
N3 N 0.76278(5) 0.04440(4) 0.51705(4) 0.02244(6) Uani 1 1 d . . .
C2 C 0.68701(6) 0.11196(4) 0.43426(5) 0.02315(7) Uani 1 1 d . . .
C4 C 0.73288(7) -0.06898(4) 0.48755(5) 0.02527(8) Uani 1 1 d . . .
C5 C 0.63694(7) -0.06935(5) 0.38486(5) 0.02665(9) Uani 1 1 d . . .
C6 C 0.51109(7) 0.08287(7) 0.24586(6) 0.03284(11) Uani 1 1 d . . .
C7 C 0.61421(8) 0.12584(5) 0.13931(5) 0.02843(9) Uani 1 1 d . . .
C8 C 0.71486(8) 0.03256(5) 0.07956(6) 0.02936(10) Uani 1 1 d . . .
C9 C 0.81275(11) 0.07827(9) -0.02786(7) 0.04352(17) Uani 1 1 d . . .
C10 C 0.69216(9) 0.23836(5) 0.43512(7) 0.03307(12) Uani 1 1 d . . .
C11 C 0.86068(8) 0.08501(6) 0.62241(6) 0.03027(10) Uani 1 1 d . . .
H4 H 0.7711(13) -0.1291(10) 0.5384(10) 0.040(3) Uiso 1 1 d . . .
H5 H 0.5916(12) -0.1341(10) 0.3375(10) 0.036(3) Uiso 1 1 d . . .
H6A H 0.4375(14) 0.1356(10) 0.2728(11) 0.044(3) Uiso 1 1 d . . .
H6B H 0.4480(13) 0.0179(11) 0.2185(11) 0.045(3) Uiso 1 1 d . . .
H7A H 0.6860(14) 0.1876(9) 0.1713(11) 0.040(3) Uiso 1 1 d . . .
H7B H 0.5408(12) 0.1595(9) 0.0741(10) 0.034(2) Uiso 1 1 d . . .
H8A H 0.7856(13) -0.0007(9) 0.1415(11) 0.040(3) Uiso 1 1 d . . .
H8B H 0.6411(13) -0.0305(9) 0.0527(10) 0.040(3) Uiso 1 1 d . . .
H9A H 0.8654(17) 0.0191(11) -0.0712(13) 0.060(4) Uiso 1 1 d . . .
H9B H 0.8902(17) 0.1322(12) 0.0015(13) 0.061(4) Uiso 1 1 d . . .
H9C H 0.7440(14) 0.1183(11) -0.0848(11) 0.048(3) Uiso 1 1 d . . .
H10A H 0.6087(15) 0.2674(10) 0.3811(11) 0.046(3) Uiso 1 1 d . . .
H10B H 0.7946(16) 0.2619(11) 0.4029(12) 0.051(3) Uiso 1 1 d . . .
H10C H 0.6758(14) 0.2629(10) 0.5185(11) 0.043(3) Uiso 1 1 d . . .
H11A H 0.7987(13) 0.1364(9) 0.6698(10) 0.039(3) Uiso 1 1 d . . .
H11B H 0.8943(14) 0.0197(10) 0.6718(11) 0.044(3) Uiso 1 1 d . . .
H11C H 0.9528(13) 0.1233(10) 0.5893(10) 0.039(3) Uiso 1 1 d . . .


_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 1.3395(7) . ?
N1 C5 1.3850(7) . ?
N1 C6 1.4720(8) . ?
N3 C2 1.3388(7) . ?
N3 C4 1.3830(7) . ?
N3 C11 1.4628(7) . ?
C2 C10 1.4766(8) . ?
C4 C5 1.3512(8) . ?
C4 H4 0.941(12) . ?
C5 H5 0.983(11) . ?
C6 C7 1.5212(10) . ?
C6 H6A 0.917(12) . ?
C6 H6B 0.966(12) . ?
C7 C8 1.5198(8) . ?
C7 H7A 0.994(11) . ?
C7 H7B 1.002(10) . ?
C8 C9 1.5149(10) . ?
C8 H8A 0.963(11) . ?
C8 H8B 0.999(11) . ?
C9 H9A 0.943(14) . ?
C9 H9B 0.952(14) . ?
C9 H9C 0.953(12) . ?
C10 H10A 0.960(13) . ?
C10 H10B 0.963(13) . ?
C10 H10C 0.950(12) . ?
C11 H11A 0.944(11) . ?
C11 H11B 0.967(12) . ?
C11 H11C 0.959(11) . ?

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 109.17(4) . . ?
C2 N1 C6 125.64(5) . . ?
C5 N1 C6 125.19(5) . . ?
C2 N3 C4 109.32(4) . . ?
C2 N3 C11 124.98(5) . . ?
C4 N3 C11 125.69(5) . . ?
N3 C2 N1 107.52(4) . . ?
N3 C2 C10 124.85(5) . . ?
N1 C2 C10 127.62(5) . . ?
C5 C4 N3 106.97(5) . . ?
C5 C4 H4 131.4(7) . . ?
N3 C4 H4 121.5(7) . . ?
C4 C5 N1 107.02(5) . . ?
C4 C5 H5 129.9(6) . . ?
N1 C5 H5 123.1(6) . . ?
N1 C6 C7 112.02(5) . . ?
N1 C6 H6A 109.1(7) . . ?
C7 C6 H6A 113.6(7) . . ?
N1 C6 H6B 106.7(7) . . ?
C7 C6 H6B 109.9(7) . . ?
H6A C6 H6B 105.1(10) . . ?
C8 C7 C6 113.46(5) . . ?
C8 C7 H7A 109.5(6) . . ?
C6 C7 H7A 108.8(7) . . ?
C8 C7 H7B 108.8(6) . . ?
C6 C7 H7B 107.9(6) . . ?
H7A C7 H7B 108.3(9) . . ?
C9 C8 C7 111.80(6) . . ?
C9 C8 H8A 109.6(7) . . ?
C7 C8 H8A 109.5(7) . . ?
C9 C8 H8B 112.0(6) . . ?
C7 C8 H8B 108.1(6) . . ?
H8A C8 H8B 105.6(9) . . ?
C8 C9 H9A 111.9(8) . . ?
C8 C9 H9B 110.5(9) . . ?
H9A C9 H9B 109.3(12) . . ?
C8 C9 H9C 109.6(7) . . ?
H9A C9 H9C 108.9(11) . . ?
H9B C9 H9C 106.6(11) . . ?
C2 C10 H10A 109.2(7) . . ?
C2 C10 H10B 108.0(8) . . ?
H10A C10 H10B 108.6(10) . . ?
C2 C10 H10C 107.7(7) . . ?
H10A C10 H10C 110.5(10) . . ?
H10B C10 H10C 112.8(10) . . ?
N3 C11 H11A 108.6(7) . . ?
N3 C11 H11B 108.7(7) . . ?
H11A C11 H11B 111.3(10) . . ?
N3 C11 H11C 107.8(7) . . ?
H11A C11 H11C 110.3(9) . . ?
H11B C11 H11C 110.1(9) . . ?

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
C4 N3 C2 N1 0.20(6) . . . . ?
C11 N3 C2 N1 -179.41(5) . . . . ?
C4 N3 C2 C10 -179.47(5) . . . . ?
C11 N3 C2 C10 0.93(8) . . . . ?
C5 N1 C2 N3 -0.27(6) . . . . ?
C6 N1 C2 N3 -179.59(5) . . . . ?
C5 N1 C2 C10 179.38(6) . . . . ?
C6 N1 C2 C10 0.07(9) . . . . ?
C2 N3 C4 C5 -0.05(6) . . . . ?
C11 N3 C4 C5 179.55(5) . . . . ?
N3 C4 C5 N1 -0.11(6) . . . . ?
C2 N1 C5 C4 0.24(6) . . . . ?
C6 N1 C5 C4 179.56(5) . . . . ?
C2 N1 C6 C7 74.69(7) . . . . ?
C5 N1 C6 C7 -104.52(7) . . . . ?
N1 C6 C7 C8 66.08(7) . . . . ?
C6 C7 C8 C9 178.69(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        50.00
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.048

