# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_teste1
_database_code_depnum_ccdc_archive 'CCDC 1028628'
_audit_update_record             
;
2014-12-01 deposited with the CCDC.
2015-03-03 downloaded from the CCDC.
;

_audit_creation_date             2014-12-01T16:27:43-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
        '1,8-bis(3-methylimidazolium-1-yl) octane tetrafluorborate'
;
_chemical_name_common            1,8-bis(3-methylimidazolium-1-yl)
_chemical_formula_moiety         'C16 H28 B2 F8 N4'
_chemical_formula_sum            'C16 H28 B2 F8 N4'
_chemical_formula_weight         450.04
_chemical_melting_point          none

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  -P2ybc
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                   5.4081(2)
_cell_length_b                   15.5202(8)
_cell_length_c                   13.3407(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.649(2)
_cell_angle_gamma                90
_cell_volume                     1100.46(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6300
_cell_measurement_theta_min      2.6245
_cell_measurement_theta_max      23.251

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.36
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             468
_exptl_special_details           
;
'XPREP (Bruker, 2006) was used to perform the Gaussian absorption
        correction based on the face-indexed crystal size'
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   XPREP
_exptl_absorpt_correction_T_min  0.9305
_exptl_absorpt_correction_T_max  0.9553

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean none
_diffrn_measurement_device_type  'X8 APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_number            29502
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         27.19
_diffrn_reflns_theta_full        27.19
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_reflns_number_total             2421
_reflns_number_gt                1582
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'BRUKER APEX-II'
_computing_cell_refinement       'BRUKER SANT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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 > 2σ(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)+(0.1224P)²+0.3187P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.007(7)
_refine_ls_number_reflns         2421
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0974
_refine_ls_R_factor_gt           0.0686
_refine_ls_wR_factor_ref         0.2399
_refine_ls_wR_factor_gt          0.2104
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.34
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.041

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
F F 0.0171 0.0103 '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'

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
C31 C 0.3429(8) 1.2664(2) 0.9448(3) 0.1072(12) Uani 1 1 d . . .
H31A H 0.2341 1.2613 0.9938 0.161 Uiso 1 1 calc R . .
H31B H 0.266 1.3032 0.89 0.161 Uiso 1 1 calc R . .
H31C H 0.5009 1.2906 0.9771 0.161 Uiso 1 1 calc R . .
N3 N 0.3850(4) 1.18111(12) 0.90439(16) 0.0709(6) Uani 1 1 d . . .
C2 C 0.5246(5) 1.16499(15) 0.83610(19) 0.0681(7) Uani 1 1 d . . .
H2 H 0.6088 1.2061 0.8043 0.082 Uiso 1 1 calc R . .
N1 N 0.5266(3) 1.08124(12) 0.81964(14) 0.0598(5) Uani 1 1 d . . .
C11 C 0.6620(5) 1.03777(18) 0.7488(2) 0.0742(7) Uani 1 1 d . . .
H11A H 0.7929 1.0017 0.787 0.089 Uiso 1 1 calc R . .
H11B H 0.742 1.0805 0.7124 0.089 Uiso 1 1 calc R . .
C12 C 0.4879(4) 0.98304(16) 0.67321(19) 0.0647(7) Uani 1 1 d . . .
H12A H 0.5866 0.9533 0.6301 0.078 Uiso 1 1 calc R . .
H12B H 0.4122 0.9396 0.7103 0.078 Uiso 1 1 calc R . .
C13 C 0.2814(4) 1.03265(14) 0.60623(17) 0.0603(6) Uani 1 1 d . . .
H13A H 0.3564 1.0742 0.5665 0.072 Uiso 1 1 calc R . .
H13B H 0.1865 1.0644 0.6491 0.072 Uiso 1 1 calc R . .
C14 C 0.1028(4) 0.97562(14) 0.53432(17) 0.0595(6) Uani 1 1 d . . .
H14A H 0.1985 0.9432 0.4924 0.071 Uiso 1 1 calc R . .
H14B H 0.0264 0.9346 0.5742 0.071 Uiso 1 1 calc R . .
C5 C 0.3766(5) 1.04354(16) 0.87974(19) 0.0712(7) Uani 1 1 d . . .
H5 H 0.3421 0.985 0.8832 0.085 Uiso 1 1 calc R . .
C4 C 0.2893(6) 1.10620(18) 0.93234(19) 0.0752(7) Uani 1 1 d . . .
H4 H 0.183 1.0996 0.9792 0.09 Uiso 1 1 calc R . .
F1 F 0.7876(8) 0.7964(6) 0.8209(4) 0.153(3) Uani 0.633(17) 1 d P A 1
F1A F 0.836(5) 0.8349(16) 0.8111(16) 0.281(11) Uani 0.367(17) 1 d P A 2
B B 1.0426(6) 0.8001(2) 0.8373(3) 0.0747(9) Uani 1 1 d . . .
F2 F 1.1305(15) 0.8547(3) 0.9085(6) 0.147(3) Uani 0.67(2) 1 d P A 1
F2A F 1.119(3) 0.822(2) 0.9344(13) 0.229(10) Uani 0.33(2) 1 d P A 2
F3 F 1.1152(15) 0.8313(7) 0.7508(5) 0.173(4) Uani 0.62(2) 1 d P A 1
F3A F 1.181(4) 0.7980(13) 0.7741(18) 0.279(11) Uani 0.38(2) 1 d P A 2
F4 F 1.0967(8) 0.72056(19) 0.8542(4) 0.2189(19) Uani 1 1 d . A .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C31 N3 1.463(4) . ?
C31 H31A 0.96 . ?
C31 H31B 0.96 . ?
C31 H31C 0.96 . ?
N3 C2 1.310(3) . ?
N3 C4 1.353(3) . ?
C2 N1 1.319(3) . ?
C2 H2 0.93 . ?
N1 C5 1.372(3) . ?
N1 C11 1.463(3) . ?
C11 C12 1.508(3) . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C12 C13 1.507(3) . ?
C12 H12A 0.97 . ?
C12 H12B 0.97 . ?
C13 C14 1.515(3) . ?
C13 H13A 0.97 . ?
C13 H13B 0.97 . ?
C14 C14 1.507(4) 3_576 ?
C14 H14A 0.97 . ?
C14 H14B 0.97 . ?
C5 C4 1.335(4) . ?
C5 H5 0.93 . ?
C4 H4 0.93 . ?
F1 B 1.357(5) . ?
F1A B 1.234(13) . ?
B F3A 1.228(12) . ?
B F4 1.279(4) . ?
B F2 1.297(6) . ?
B F2A 1.329(12) . ?
B F3 1.374(6) . ?
F3A F4 1.72(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
N3 C31 H31A 109.5 . . ?
N3 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
N3 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C2 N3 C4 109.1(2) . . ?
C2 N3 C31 125.3(3) . . ?
C4 N3 C31 125.6(3) . . ?
N3 C2 N1 109.1(2) . . ?
N3 C2 H2 125.4 . . ?
N1 C2 H2 125.4 . . ?
C2 N1 C5 107.4(2) . . ?
C2 N1 C11 125.6(2) . . ?
C5 N1 C11 127.0(2) . . ?
N1 C11 C12 111.50(19) . . ?
N1 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
N1 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 108 . . ?
C13 C12 C11 114.3(2) . . ?
C13 C12 H12A 108.7 . . ?
C11 C12 H12A 108.7 . . ?
C13 C12 H12B 108.7 . . ?
C11 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C12 C13 C14 113.15(19) . . ?
C12 C13 H13A 108.9 . . ?
C14 C13 H13A 108.9 . . ?
C12 C13 H13B 108.9 . . ?
C14 C13 H13B 108.9 . . ?
H13A C13 H13B 107.8 . . ?
C14 C14 C13 113.8(2) 3_576 . ?
C14 C14 H14A 108.8 3_576 . ?
C13 C14 H14A 108.8 . . ?
C14 C14 H14B 108.8 3_576 . ?
C13 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C4 C5 N1 107.5(2) . . ?
C4 C5 H5 126.2 . . ?
N1 C5 H5 126.2 . . ?
C5 C4 N3 106.9(2) . . ?
C5 C4 H4 126.6 . . ?
N3 C4 H4 126.6 . . ?
F3A B F1A 117.1(18) . . ?
F3A B F4 86.9(11) . . ?
F1A B F4 129.7(16) . . ?
F3A B F2 109.4(11) . . ?
F1A B F2 96.4(12) . . ?
F4 B F2 117.5(5) . . ?
F3A B F2A 123.7(15) . . ?
F1A B F2A 105.5(12) . . ?
F4 B F2A 93.1(16) . . ?
F2 B F2A 27.5(16) . . ?
F3A B F1 128.3(13) . . ?
F1A B F1 29.6(14) . . ?
F4 B F1 100.4(5) . . ?
F2 B F1 111.7(5) . . ?
F2A B F1 107.0(7) . . ?
F3A B F3 29.2(10) . . ?
F1A B F3 89.6(14) . . ?
F4 B F3 113.4(6) . . ?
F2 B F3 105.1(5) . . ?
F2A B F3 129.9(15) . . ?
F1 B F3 108.6(5) . . ?
B F3A F4 47.8(8) . . ?
B F4 F3A 45.3(4) . . ?

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 -1.0(3) . . . . ?
C31 N3 C2 N1 178.2(3) . . . . ?
N3 C2 N1 C5 1.0(3) . . . . ?
N3 C2 N1 C11 -179.8(2) . . . . ?
C2 N1 C11 C12 -124.6(3) . . . . ?
C5 N1 C11 C12 54.4(3) . . . . ?
N1 C11 C12 C13 61.2(3) . . . . ?
C11 C12 C13 C14 -177.4(2) . . . . ?
C12 C13 C14 C14 -179.1(2) . . . 3_576 ?
C2 N1 C5 C4 -0.7(3) . . . . ?
C11 N1 C5 C4 -179.9(2) . . . . ?
N1 C5 C4 N3 0.1(3) . . . . ?
C2 N3 C4 C5 0.6(3) . . . . ?
C31 N3 C4 C5 -178.6(3) . . . . ?
F1A B F3A F4 -133.7(16) . . . . ?
F2 B F3A F4 118.1(7) . . . . ?
F2A B F3A F4 92(2) . . . . ?
F1 B F3A F4 -100.8(10) . . . . ?
F3 B F3A F4 -155(2) . . . . ?
F1A B F4 F3A 123.2(18) . . . . ?
F2 B F4 F3A -110.3(13) . . . . ?
F2A B F4 F3A -123.6(15) . . . . ?
F1 B F4 F3A 128.4(13) . . . . ?
F3 B F4 F3A 12.7(13) . . . . ?

# END of CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
