# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1400362'
_audit_update_record             
;
2015-05-12 deposited with the CCDC.
2015-06-18 downloaded from the CCDC.
;

_audit_creation_date             2014-02-21T14:10:13-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        'N-methylquinoxalinium tetrafluoroborate'
_chemical_formula_moiety         'C9 H9 N2, B F4'
_chemical_formula_sum            'C9 H9 B F4 N2'
_chemical_formula_weight         231.99
_chemical_compound_source        'synthesis as described'

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/a'
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, z'

_cell_length_a                   13.372(2)
_cell_length_b                   6.2221(9)
_cell_length_c                   13.8278(19)
_cell_angle_alpha                90
_cell_angle_beta                 112.232(11)
_cell_angle_gamma                90
_cell_volume                     1064.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1470
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      21.32
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.204
_exptl_crystal_size_mid          0.176
_exptl_crystal_size_min          0.102
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
7 0 -1 0.071

_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_type   none

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

_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_detector                 'image plate ( 34 cm diameter )'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_source                   'sealed X-ray tube, 12 x 0.4 mm fine focus'
_diffrn_source_voltage           50
_diffrn_source_current           40
_diffrn_source_power             2.000
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'planar graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    '0.3 mm, multiple pinhole'
_diffrn_ambient_temperature      293
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_details      
; 130 frames, detector distance = 115 mm
;
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_number            4693
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.066
_diffrn_reflns_theta_max         27.398
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.974
_reflns_number_total             2357
_reflns_number_gt                707
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0423P)²] 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       0.028(4)
_refine_ls_number_reflns         2357
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1415
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.0992
_refine_ls_wR_factor_gt          0.0764
_refine_ls_goodness_of_fit_ref   0.716
_refine_ls_restrained_S_all      0.716
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.082
_refine_diff_density_min         -0.074
_refine_diff_density_rms         0.018

#----------------------------------------------------------------------------#
#                   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
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4436(2) 0.0859(5) 0.0850(2) 0.1379(11) Uani 1 d . .
H1A H 0.3923 0.1519 0.0234 0.207 Uiso 1 calc . .
H1B H 0.422 -0.0595 0.09 0.207 Uiso 1 calc . .
H1C H 0.5138 0.0865 0.0812 0.207 Uiso 1 calc . .
C2 C 0.51092(16) 0.1408(4) 0.2769(2) 0.0856(6) Uani 1 d . .
C3 C 0.5727(2) -0.0443(4) 0.2935(3) 0.1170(9) Uani 1 d . .
H3 H 0.5725 -0.1274 0.2375 0.14 Uiso 1 calc . .
C4 C 0.6337(2) -0.1021(5) 0.3935(4) 0.1406(12) Uani 1 d . .
H4 H 0.675 -0.2268 0.4054 0.169 Uiso 1 calc . .
C5 C 0.6356(2) 0.0184(6) 0.4765(3) 0.1328(10) Uani 1 d . .
H5 H 0.6784 -0.0249 0.5439 0.159 Uiso 1 calc . .
C6 C 0.5767(2) 0.1985(5) 0.4621(2) 0.1166(8) Uani 1 d . .
H6 H 0.5792 0.28 0.5194 0.14 Uiso 1 calc . .
C7 C 0.51133(17) 0.2642(4) 0.3608(2) 0.0903(6) Uani 1 d . .
C8 C 0.3923(2) 0.4979(4) 0.2523(3) 0.1192(9) Uani 1 d . .
H8 H 0.3497 0.6206 0.2413 0.143 Uiso 1 calc . .
C9 C 0.38936(19) 0.3816(5) 0.1652(2) 0.1074(8) Uani 1 d . .
H9 H 0.3464 0.4276 0.0984 0.129 Uiso 1 calc . .
N1 N 0.44748(16) 0.2075(4) 0.17824(17) 0.0951(6) Uani 1 d . .
N2 N 0.45079(18) 0.4450(3) 0.3476(2) 0.1136(7) Uani 1 d . .
F1A F 0.5868(4) 0.5765(10) 0.1375(4) 0.132(2) Uani 0.73(3) d . .
F1B F 0.604(3) 0.511(7) 0.176(5) 0.264(12) Uani 0.27(3) d . .
F2A F 0.7269(17) 0.451(3) 0.2513(7) 0.263(5) Uani 0.57(3) d . .
F2B F 0.7750(9) 0.4962(11) 0.2483(7) 0.138(4) Uani 0.43(3) d . .
F3A F 0.7261(10) 0.655(2) 0.1372(16) 0.274(6) Uani 0.43(2) d . .
F3B F 0.7345(3) 0.6009(14) 0.1001(6) 0.152(3) Uani 0.57(2) d . .
F4A F 0.6742(6) 0.329(2) 0.0882(10) 0.166(4) Uani 0.66(3) d . .
F4B F 0.6773(10) 0.2716(18) 0.144(3) 0.157(7) Uani 0.34(3) d . .
B1 B 0.6847(2) 0.4896(5) 0.1564(3) 0.0834(7) Uani 1 d . .



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

_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 1.478(3) . ?
C1 H1A 0.96 . ?
C1 H1B 0.96 . ?
C1 H1C 0.96 . ?
C2 N1 1.370(3) . ?
C2 C3 1.385(3) . ?
C2 C7 1.390(3) . ?
C3 C4 1.361(4) . ?
C3 H3 0.93 . ?
C4 C5 1.363(4) . ?
C4 H4 0.93 . ?
C5 C6 1.341(4) . ?
C5 H5 0.93 . ?
C6 C7 1.402(3) . ?
C6 H6 0.93 . ?
C7 N2 1.357(3) . ?
C8 N2 1.295(3) . ?
C8 C9 1.392(4) . ?
C8 H8 0.93 . ?
C9 N1 1.305(3) . ?
C9 H9 0.93 . ?
F1A F1B 0.64(7) . ?
F1A B1 1.348(5) . ?
F1B B1 1.220(15) . ?
F1B F2A 1.62(6) . ?
F2A F2B 0.719(17) . ?
F2A B1 1.240(9) . ?
F2A F4B 1.77(3) . ?
F2B B1 1.383(9) . ?
F2B F3A 1.732(18) . ?
F3A F3B 0.659(19) . ?
F3A B1 1.244(11) . ?
F3B B1 1.387(6) . ?
F4A F4B 0.838(17) . ?
F4A B1 1.344(7) . ?
F4B B1 1.366(12) . ?

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 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 121.5(3) . . ?
N1 C2 C7 118.0(2) . . ?
C3 C2 C7 120.5(3) . . ?
C4 C3 C2 118.6(3) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C3 C4 C5 121.6(3) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C7 120.1(3) . . ?
C5 C6 H6 120 . . ?
C7 C6 H6 120 . . ?
N2 C7 C2 122.1(2) . . ?
N2 C7 C6 119.4(3) . . ?
C2 C7 C6 118.5(3) . . ?
N2 C8 C9 123.8(3) . . ?
N2 C8 H8 118.1 . . ?
C9 C8 H8 118.1 . . ?
N1 C9 C8 119.4(3) . . ?
N1 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C9 N1 C2 120.1(2) . . ?
C9 N1 C1 118.8(3) . . ?
C2 N1 C1 121.2(2) . . ?
C8 N2 C7 116.6(2) . . ?
F1B F1A B1 64.6(17) . . ?
F1A F1B B1 87(4) . . ?
F1A F1B F2A 129(2) . . ?
B1 F1B F2A 49.3(18) . . ?
F2B F2A B1 85.4(15) . . ?
F2B F2A F1B 126(2) . . ?
B1 F2A F1B 48.2(18) . . ?
F2B F2A F4B 105.1(14) . . ?
B1 F2A F4B 50.3(9) . . ?
F1B F2A F4B 69.1(11) . . ?
F2A F2B B1 63.4(11) . . ?
F2A F2B F3A 103.4(15) . . ?
B1 F2B F3A 45.4(4) . . ?
F3B F3A B1 87.9(14) . . ?
F3B F3A F2B 106.3(19) . . ?
B1 F3A F2B 52.3(7) . . ?
F3A F3B B1 63.7(12) . . ?
F4B F4A B1 73.4(13) . . ?
F4A F4B B1 70.5(11) . . ?
F4A F4B F2A 112.1(17) . . ?
B1 F4B F2A 44.3(8) . . ?
F1B B1 F2A 82(4) . . ?
F1B B1 F3A 117(2) . . ?
F2A B1 F3A 109.1(15) . . ?
F1B B1 F4A 112.0(11) . . ?
F2A B1 F4A 118.8(10) . . ?
F3A B1 F4A 113.7(13) . . ?
F1B B1 F1A 28(3) . . ?
F2A B1 F1A 107.6(8) . . ?
F3A B1 F1A 96.0(9) . . ?
F4A B1 F1A 109.0(4) . . ?
F1B B1 F4B 96.2(18) . . ?
F2A B1 F4B 85.4(16) . . ?
F3A B1 F4B 144.3(14) . . ?
F4A B1 F4B 36.0(8) . . ?
F1A B1 F4B 110.8(6) . . ?
F1B B1 F2B 109(3) . . ?
F2A B1 F2B 31.2(8) . . ?
F3A B1 F2B 82.3(8) . . ?
F4A B1 F2B 119.4(6) . . ?
F1A B1 F2B 127.7(5) . . ?
F4B B1 F2B 98.1(11) . . ?
F1B B1 F3B 137(3) . . ?
F2A B1 F3B 124.7(13) . . ?
F3A B1 F3B 28.4(9) . . ?
F4A B1 F3B 85.5(9) . . ?
F1A B1 F3B 109.2(4) . . ?
F4B B1 F3B 117.0(12) . . ?
F2B B1 F3B 93.6(6) . . ?

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 C2 C3 C4 -179.8(2) . . . . ?
C7 C2 C3 C4 -0.1(3) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
C3 C4 C5 C6 0.3(5) . . . . ?
C4 C5 C6 C7 0.5(4) . . . . ?
N1 C2 C7 N2 0.5(3) . . . . ?
C3 C2 C7 N2 -179.13(19) . . . . ?
N1 C2 C7 C6 -179.44(18) . . . . ?
C3 C2 C7 C6 0.9(3) . . . . ?
C5 C6 C7 N2 178.9(2) . . . . ?
C5 C6 C7 C2 -1.1(3) . . . . ?
N2 C8 C9 N1 0.6(4) . . . . ?
C8 C9 N1 C2 -0.2(3) . . . . ?
C8 C9 N1 C1 -179.97(19) . . . . ?
C3 C2 N1 C9 179.31(19) . . . . ?
C7 C2 N1 C9 -0.3(2) . . . . ?
C3 C2 N1 C1 -0.9(3) . . . . ?
C7 C2 N1 C1 179.43(18) . . . . ?
C9 C8 N2 C7 -0.5(4) . . . . ?
C2 C7 N2 C8 -0.1(3) . . . . ?
C6 C7 N2 C8 179.8(2) . . . . ?
B1 F1A F1B F2A 27(2) . . . . ?
F1A F1B F2A F2B 2(5) . . . . ?
B1 F1B F2A F2B 39(2) . . . . ?
F1A F1B F2A B1 -37(3) . . . . ?
F1A F1B F2A F4B -92(4) . . . . ?
B1 F1B F2A F4B -54.8(10) . . . . ?
F1B F2A F2B B1 -28.2(15) . . . . ?
F4B F2A F2B B1 46.7(9) . . . . ?
B1 F2A F2B F3A 22.1(12) . . . . ?
F1B F2A F2B F3A -6(2) . . . . ?
F4B F2A F2B F3A 68.8(14) . . . . ?
F2A F2B F3A F3B -102(2) . . . . ?
B1 F2B F3A F3B -74.1(13) . . . . ?
F2A F2B F3A B1 -28.2(16) . . . . ?
F2B F3A F3B B1 49.6(7) . . . . ?
B1 F4A F4B F2A -15.8(10) . . . . ?
F2B F2A F4B F4A -49(2) . . . . ?
B1 F2A F4B F4A 21.6(15) . . . . ?
F1B F2A F4B F4A 74(3) . . . . ?
F2B F2A F4B B1 -70.6(16) . . . . ?
F1B F2A F4B B1 52(2) . . . . ?
F1A F1B B1 F2A 152(2) . . . . ?
F1A F1B B1 F3A 45(4) . . . . ?
F2A F1B B1 F3A -108(2) . . . . ?
F1A F1B B1 F4A -90(2) . . . . ?
F2A F1B B1 F4A 118.1(18) . . . . ?
F2A F1B B1 F1A -152(2) . . . . ?
F1A F1B B1 F4B -123(2) . . . . ?
F2A F1B B1 F4B 84.5(17) . . . . ?
F1A F1B B1 F2B 136(2) . . . . ?
F2A F1B B1 F2B -16.4(13) . . . . ?
F1A F1B B1 F3B 18(4) . . . . ?
F2A F1B B1 F3B -134(2) . . . . ?
F2B F2A B1 F1B -149(2) . . . . ?
F4B F2A B1 F1B 96.9(16) . . . . ?
F2B F2A B1 F3A -32.6(17) . . . . ?
F1B F2A B1 F3A 116.5(17) . . . . ?
F4B F2A B1 F3A -146.6(11) . . . . ?
F2B F2A B1 F4A 99.9(19) . . . . ?
F1B F2A B1 F4A -111.0(17) . . . . ?
F4B F2A B1 F4A -14.0(11) . . . . ?
F2B F2A B1 F1A -135.6(12) . . . . ?
F1B F2A B1 F1A 13.5(15) . . . . ?
F4B F2A B1 F1A 110.4(7) . . . . ?
F2B F2A B1 F4B 114.0(14) . . . . ?
F1B F2A B1 F4B -96.9(16) . . . . ?
F1B F2A B1 F2B 149(2) . . . . ?
F4B F2A B1 F2B -114.0(14) . . . . ?
F2B F2A B1 F3B -5.9(18) . . . . ?
F1B F2A B1 F3B 143.2(16) . . . . ?
F4B F2A B1 F3B -119.9(9) . . . . ?
F3B F3A B1 F1B -140(3) . . . . ?
F2B F3A B1 F1B 108(3) . . . . ?
F3B F3A B1 F2A 128.9(15) . . . . ?
F2B F3A B1 F2A 16.4(7) . . . . ?
F3B F3A B1 F4A -6.2(19) . . . . ?
F2B F3A B1 F4A -118.8(7) . . . . ?
F3B F3A B1 F1A -120.1(14) . . . . ?
F2B F3A B1 F1A 127.4(5) . . . . ?
F3B F3A B1 F4B 19(3) . . . . ?
F2B F3A B1 F4B -93(2) . . . . ?
F3B F3A B1 F2B 112.6(16) . . . . ?
F2B F3A B1 F3B -112.6(16) . . . . ?
F4B F4A B1 F1B -69(4) . . . . ?
F4B F4A B1 F2A 24(2) . . . . ?
F4B F4A B1 F3A 154.7(14) . . . . ?
F4B F4A B1 F1A -99.5(12) . . . . ?
F4B F4A B1 F2B 60.1(16) . . . . ?
F4B F4A B1 F3B 151.8(12) . . . . ?
F1B F1A B1 F2A -29(3) . . . . ?
F1B F1A B1 F3A -141(3) . . . . ?
F1B F1A B1 F4A 101(3) . . . . ?
F1B F1A B1 F4B 63(3) . . . . ?
F1B F1A B1 F2B -56(3) . . . . ?
F1B F1A B1 F3B -167(2) . . . . ?
F4A F4B B1 F1B 119(3) . . . . ?
F2A F4B B1 F1B -82(3) . . . . ?
F4A F4B B1 F2A -158.8(16) . . . . ?
F4A F4B B1 F3A -42(3) . . . . ?
F2A F4B B1 F3A 117(2) . . . . ?
F2A F4B B1 F4A 158.8(16) . . . . ?
F4A F4B B1 F1A 94.1(12) . . . . ?
F2A F4B B1 F1A -107.1(11) . . . . ?
F4A F4B B1 F2B -130.2(13) . . . . ?
F2A F4B B1 F2B 28.6(7) . . . . ?
F4A F4B B1 F3B -31.9(15) . . . . ?
F2A F4B B1 F3B 126.9(12) . . . . ?
F2A F2B B1 F1B 33(3) . . . . ?
F3A F2B B1 F1B -116(2) . . . . ?
F3A F2B B1 F2A -149.1(18) . . . . ?
F2A F2B B1 F3A 149.1(18) . . . . ?
F2A F2B B1 F4A -98.0(19) . . . . ?
F3A F2B B1 F4A 113.0(14) . . . . ?
F2A F2B B1 F1A 57.4(15) . . . . ?
F3A F2B B1 F1A -91.7(12) . . . . ?
F2A F2B B1 F4B -66.9(18) . . . . ?
F3A F2B B1 F4B 144.0(14) . . . . ?
F2A F2B B1 F3B 175.1(15) . . . . ?
F3A F2B B1 F3B 26.1(9) . . . . ?
F3A F3B B1 F1B 57(3) . . . . ?
F3A F3B B1 F2A -63.4(18) . . . . ?
F3A F3B B1 F4A 174.3(17) . . . . ?
F3A F3B B1 F1A 65.7(16) . . . . ?
F3A F3B B1 F4B -167.5(19) . . . . ?
F3A F3B B1 F2B -66.5(17) . . . . ?


# END of CIF
_chemical_name_common            (MQ)BF4
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1400365'
_audit_update_record             
;
2015-05-12 deposited with the CCDC.
2015-06-18 downloaded from the CCDC.
;

_audit_creation_date             2014-02-04T10:16:19-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        '(MQ)[CuBr2] (MQ=N-methylquinoxalinium)'
_chemical_formula_moiety         'Br2 Cu, C9 H9 N2'
_chemical_formula_sum            'C9 H9 Br2 Cu N2'
_chemical_formula_weight         368.54
_chemical_compound_source        'synthesis as described'

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/m'
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_Int_Tables_number      12
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   15.373(2)
_cell_length_b                   6.4099(7)
_cell_length_c                   10.9646(18)
_cell_angle_alpha                90
_cell_angle_beta                 96.692(12)
_cell_angle_gamma                90
_cell_volume                     1073.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2575
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      27.91
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.362
_exptl_crystal_size_mid          0.185
_exptl_crystal_size_min          0.081
_exptl_crystal_density_diffrn    2.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    9.441
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'
_exptl_absorpt_correction_T_min  0.1832
_exptl_absorpt_correction_T_max  0.4145
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
12 0 -1 0.1160
12 5 -1 0.1312
24 10 15 0.1051
8 0 5 0.1148
24 -10 15 0.1267
12 -5 -1 0.1342
24 -10 -19 0.0946
24 0 -19 0.1104
24 10 -19 0.1326
0 1 0 0.1353
0 10 17 0.0803
0 0 1 0.0504
0 -10 17 0.1002
-12 0 1 0.1487
-12 -5 1 0.1074
-24 -10 -15 0.1094
-8 0 -5 0.1265
-24 10 -15 0.1016
-12 5 1 0.1046
-24 10 19 0.0979
-24 0 19 0.1274
-24 -10 19 0.1122
0 -1 0 0.1322
0 -10 -17 0.0995
0 0 -1 0.0469
0 10 -17 0.1240

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

_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_detector                 'image plate ( 34 cm diameter )'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_source                   'sealed X-ray tube, 12 x 0.4 mm fine focus'
_diffrn_source_voltage           50
_diffrn_source_current           40
_diffrn_source_power             2.000
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'planar graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    '0.5 mm, multiple pinhole'
_diffrn_ambient_temperature      293
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_details      
; 135 frames, detector distance = 115 mm
;
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_number            2530
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.447
_diffrn_reflns_theta_max         27.308
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.949
_diffrn_measured_fraction_theta_max 0.955
_diffrn_reflns_Laue_measured_fraction_full 0.949
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_point_group_measured_fraction_full 0.949
_diffrn_reflns_point_group_measured_fraction_max 0.955
_reflns_number_total             1265
_reflns_number_gt                1133
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_hydrogens   mixed

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

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0462P)²+0.6428P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.012(2)
_refine_ls_number_reflns         1265
_refine_ls_number_parameters     92
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.029
_refine_ls_wR_factor_ref         0.0912
_refine_ls_wR_factor_gt          0.0792
_refine_ls_goodness_of_fit_ref   1.322
_refine_ls_restrained_S_all      1.322
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.39
_refine_diff_density_min         -0.582
_refine_diff_density_rms         0.075

#----------------------------------------------------------------------------#
#                   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'
Cu Cu 0.3201 1.2651 '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'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7633(4) 0.5 0.8930(5) 0.0591(12) Uani 1 d . .
C2 C 0.7516(3) 0.5 0.6666(4) 0.0464(9) Uani 1 d . .
C3 C 0.8428(3) 0.5 0.6711(5) 0.0539(11) Uani 1 d . .
H3 H 0.8783 0.5 0.7459 0.065 Uiso 1 calc . .
C4 C 0.8783(4) 0.5 0.5629(6) 0.0642(13) Uani 1 d . .
H4 H 0.939 0.5 0.5647 0.077 Uiso 1 calc . .
C5 C 0.8264(4) 0.5 0.4487(6) 0.0674(14) Uani 1 d . .
H5 H 0.8527 0.5 0.3766 0.081 Uiso 1 calc . .
C6 C 0.7373(4) 0.5 0.4436(5) 0.0606(12) Uani 1 d . .
H6 H 0.7028 0.5 0.3681 0.073 Uiso 1 calc . .
C7 C 0.6979(3) 0.5 0.5528(5) 0.0529(10) Uani 1 d . .
C8 C 0.5741(3) 0.5 0.6494(6) 0.0618(12) Uani 1 d . .
H8 H 0.5134 0.5 0.6464 0.074 Uiso 1 calc . .
C9 C 0.6240(3) 0.5 0.7645(5) 0.0559(11) Uani 1 d . .
H9 H 0.5965 0.5 0.8357 0.067 Uiso 1 calc . .
N1 N 0.7100(2) 0.5 0.7716(4) 0.0485(8) Uani 1 d . .
N2 N 0.6083(3) 0.5 0.5466(5) 0.0633(11) Uani 1 d . .
Cu1 Cu 1 0.73359(11) 1 0.0655(3) Uani 1 d . .
Br2 Br 0.92809(3) 0.5 1.14004(5) 0.0540(2) Uani 1 d . .
Br1 Br 0.90464(3) 1 0.87694(4) 0.0520(2) Uani 1 d . .
H1B H 0.804(3) 0.641(8) 0.904(5) 0.084(14) Uiso 1 d . .
H1C H 0.732(4) 0.5 0.942(7) 0.067(19) Uiso 1 d . .



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

_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 1.480(6) . ?
C1 H1B 1.10(5) . ?
C1 H1C 0.77(8) . ?
C2 N1 1.381(6) . ?
C2 C3 1.397(6) . ?
C2 C7 1.414(7) . ?
C3 C4 1.362(8) . ?
C3 H3 0.93 . ?
C4 C5 1.405(9) . ?
C4 H4 0.93 . ?
C5 C6 1.364(9) . ?
C5 H5 0.93 . ?
C6 C7 1.403(8) . ?
C6 H6 0.93 . ?
C7 N2 1.372(6) . ?
C8 N2 1.298(8) . ?
C8 C9 1.398(8) . ?
C8 H8 0.93 . ?
C9 N1 1.315(6) . ?
C9 H9 0.93 . ?
Cu1 Br2 2.4935(6) 5_767 ?
Cu1 Br2 2.4935(6) . ?
Cu1 Br1 2.5347(6) 5_777 ?
Cu1 Br1 2.5347(6) . ?
Cu1 Cu1 2.9946(15) 5_767 ?
Br2 Cu1 2.4934(6) 5_767 ?
Br1 Cu1 2.5347(6) 5_777 ?

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 H1B 110(3) . . ?
N1 C1 H1C 108(5) . . ?
H1B C1 H1C 109(3) . . ?
N1 C2 C3 122.1(4) . . ?
N1 C2 C7 117.1(4) . . ?
C3 C2 C7 120.8(5) . . ?
C4 C3 C2 118.1(5) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
C3 C4 C5 122.2(5) . . ?
C3 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?
C6 C5 C4 120.0(5) . . ?
C6 C5 H5 120 . . ?
C4 C5 H5 120 . . ?
C5 C6 C7 119.7(5) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
N2 C7 C6 119.2(5) . . ?
N2 C7 C2 121.6(5) . . ?
C6 C7 C2 119.2(5) . . ?
N2 C8 C9 123.3(5) . . ?
N2 C8 H8 118.3 . . ?
C9 C8 H8 118.3 . . ?
N1 C9 C8 119.6(5) . . ?
N1 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 N1 C2 120.7(4) . . ?
C9 N1 C1 120.1(5) . . ?
C2 N1 C1 119.2(4) . . ?
C8 N2 C7 117.5(5) . . ?
Br2 Cu1 Br2 106.19(3) 5_767 . ?
Br2 Cu1 Br1 117.514(17) 5_767 5_777 ?
Br2 Cu1 Br1 110.314(17) . 5_777 ?
Br2 Cu1 Br1 110.314(17) 5_767 . ?
Br2 Cu1 Br1 117.513(16) . . ?
Br1 Cu1 Br1 95.29(3) 5_777 . ?
Br2 Cu1 Cu1 53.094(15) 5_767 5_767 ?
Br2 Cu1 Cu1 53.094(16) . 5_767 ?
Br1 Cu1 Cu1 132.354(15) 5_777 5_767 ?
Br1 Cu1 Cu1 132.354(15) . 5_767 ?
Cu1 Br2 Cu1 73.81(3) 5_767 . ?
Cu1 Br1 Cu1 84.71(3) . 5_777 ?

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 C2 C3 C4 180.0000(10) . . . . ?
C7 C2 C3 C4 0.0000(10) . . . . ?
C2 C3 C4 C5 0.0000(10) . . . . ?
C3 C4 C5 C6 0.0000(10) . . . . ?
C4 C5 C6 C7 0.0000(10) . . . . ?
C5 C6 C7 N2 180.0000(10) . . . . ?
C5 C6 C7 C2 0.0000(10) . . . . ?
N1 C2 C7 N2 0.0000(10) . . . . ?
C3 C2 C7 N2 180.0000(10) . . . . ?
N1 C2 C7 C6 180.0000(10) . . . . ?
C3 C2 C7 C6 0.0000(10) . . . . ?
N2 C8 C9 N1 0.000(2) . . . . ?
C8 C9 N1 C2 0.0000(10) . . . . ?
C8 C9 N1 C1 180.0000(10) . . . . ?
C3 C2 N1 C9 180.0000(10) . . . . ?
C7 C2 N1 C9 0.0000(10) . . . . ?
C3 C2 N1 C1 0.0000(10) . . . . ?
C7 C2 N1 C1 180.0000(10) . . . . ?
C9 C8 N2 C7 0.0000(10) . . . . ?
C6 C7 N2 C8 180.0000(10) . . . . ?
C2 C7 N2 C8 0.0000(10) . . . . ?


# END of CIF
_exptl_crystal_recrystallization_method 
'vapour diffusion of MeOH in a DMSO solution'
