# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# 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 1511787'
_audit_update_record             
;
2016-10-26 deposited with the CCDC.
2017-03-15 downloaded from the CCDC.
;

_audit_creation_date             2015-08-04T16:32:50-00:00
_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,N'-dimethyl-3,3'-biquinoxalinium bis tetrafluroborate, acetonitrile"
_chemical_formula_moiety         'C18 H16 N4, 2(B F4), C2 N '
_chemical_formula_sum            'C20 H16 B2 F8 N5 '
_chemical_formula_weight         500
_chemical_compound_source        'synthesis as described'

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
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'
'-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                   19.372(2)
_cell_length_b                   12.2295(10)
_cell_length_c                   11.3742(14)
_cell_angle_alpha                90
_cell_angle_beta                 124.421(8)
_cell_angle_gamma                90
_cell_volume                     2222.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    5166
_cell_measurement_theta_min      2.09
_cell_measurement_theta_max      27.21
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            yellowish
_exptl_crystal_size_max          0.385
_exptl_crystal_size_mid          0.367
_exptl_crystal_size_min          0.344
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1012
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.137
_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    '0.5 mm, multiple pinhole'
_diffrn_ambient_temperature      291
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_details      
; 208 frames, detector distance = 115 mm
;
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_number            5009
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.097
_diffrn_reflns_theta_max         27.415
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.964
_reflns_number_total             2438
_reflns_number_gt                1793
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   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)+(0.1326P)²+0.3066P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2438
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0617
_refine_ls_wR_factor_ref         0.2111
_refine_ls_wR_factor_gt          0.1964
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_restrained_S_all      1.132
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.039

#----------------------------------------------------------------------------#
#                   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'
B B 0.0013 0.0007 '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'

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 0.63799(15) 0.36049(16) 0.7139(3) 0.0699(6) Uani 1 d . .
H1A H 0.6509 0.4325 0.6978 0.105 Uiso 1 calc . .
H1B H 0.669 0.3467 0.8145 0.105 Uiso 1 calc . .
H1C H 0.5792 0.3554 0.6734 0.105 Uiso 1 calc . .
C2 C 0.70161(11) 0.31004(14) 0.59014(18) 0.0529(4) Uani 1 d . .
H2 H 0.714 0.3836 0.5909 0.063 Uiso 1 calc . .
C3 C 0.72634(11) 0.23182(13) 0.52926(17) 0.0513(4) Uani 1 d . .
C4 C 0.66756(11) 0.09510(14) 0.58152(17) 0.0535(4) Uani 1 d . .
C5 C 0.64979(14) -0.01675(15) 0.5791(2) 0.0628(5) Uani 1 d . .
H5 H 0.6654 -0.0667 0.5364 0.075 Uiso 1 calc . .
C6 C 0.60990(14) -0.05175(17) 0.6391(2) 0.0669(5) Uani 1 d . .
H6 H 0.5981 -0.1257 0.6374 0.08 Uiso 1 calc . .
C7 C 0.58635(14) 0.02347(18) 0.7038(2) 0.0689(5) Uani 1 d . .
H7 H 0.5596 -0.0021 0.7453 0.083 Uiso 1 calc . .
C8 C 0.60148(13) 0.13218(17) 0.7077(2) 0.0638(5) Uani 1 d . .
H8 H 0.5851 0.1808 0.7504 0.077 Uiso 1 calc . .
C9 C 0.64245(11) 0.16970(14) 0.64559(17) 0.0528(4) Uani 1 d . .
C10 C 0.5 0.2969(3) 0.25 0.0783(8) Uani 1 d . .
C11 C 0.5 0.4149(3) 0.25 0.1217(17) Uani 1 d . .
N1 N 0.66110(10) 0.27841(11) 0.64567(15) 0.0531(4) Uani 1 d . .
N2 N 0.70919(10) 0.12754(12) 0.52405(15) 0.0554(4) Uani 1 d . .
N3 N 0.5 0.2058(3) 0.25 0.1145(13) Uani 1 d . .
B1 B 0.86709(18) 0.1537(2) 0.9571(2) 0.0704(6) Uani 1 d . .
F1 F 0.83730(19) 0.05982(15) 0.9715(3) 0.1401(9) Uani 1 d . .
F2A F 0.8642(5) 0.1577(5) 0.8394(6) 0.143(2) Uani 0.701(14) d . .
F2B F 0.8358(11) 0.1924(16) 0.8379(13) 0.218(11) Uani 0.299(14) d . .
F3A F 0.8095(2) 0.2321(2) 0.9432(5) 0.1073(14) Uani 0.640(8) d . .
F3B F 0.9395(7) 0.0960(11) 0.9701(17) 0.214(6) Uani 0.360(8) d . .
F4A F 0.9359(2) 0.1837(6) 1.0743(5) 0.150(2) Uani 0.735(13) d . .
F4B F 0.903(2) 0.2223(13) 1.058(2) 0.197(10) Uani 0.265(13) 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 1.484(2) . ?
C2 N1 1.313(2) . ?
C2 C3 1.414(2) . ?
C3 N2 1.311(2) . ?
C3 C3 1.473(3) 7_656 ?
C4 N2 1.353(2) . ?
C4 C5 1.407(3) . ?
C4 C9 1.414(3) . ?
C5 C6 1.358(3) . ?
C6 C7 1.406(3) . ?
C7 C8 1.357(3) . ?
C8 C9 1.405(3) . ?
C9 N1 1.377(2) . ?
C10 N3 1.115(5) . ?
C10 C11 1.442(5) . ?
B1 F2B 1.225(10) . ?
B1 F4B 1.263(10) . ?
B1 F4A 1.296(4) . ?
B1 F2A 1.309(4) . ?
B1 F1 1.336(3) . ?
B1 F3A 1.411(4) . ?
B1 F3B 1.502(10) . ?
F2A F2B 0.69(3) . ?
F2A F3B 1.568(15) . ?
F2B F3A 1.62(3) . ?
F3A F4B 1.53(3) . ?
F3B F4A 1.629(13) . ?
F4A F4B 0.72(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
N1 C2 C3 119.75(16) . . ?
N2 C3 C2 122.21(16) . . ?
N2 C3 C3 118.66(18) . 7_656 ?
C2 C3 C3 119.12(19) . 7_656 ?
N2 C4 C5 118.78(16) . . ?
N2 C4 C9 122.15(16) . . ?
C5 C4 C9 119.06(17) . . ?
C6 C5 C4 119.94(18) . . ?
C5 C6 C7 120.16(19) . . ?
C8 C7 C6 122.01(19) . . ?
C7 C8 C9 118.49(19) . . ?
N1 C9 C8 122.51(16) . . ?
N1 C9 C4 117.16(15) . . ?
C8 C9 C4 120.32(17) . . ?
N3 C10 C11 180 . . ?
C2 N1 C9 120.77(14) . . ?
C2 N1 C1 119.41(15) . . ?
C9 N1 C1 119.78(15) . . ?
C3 N2 C4 117.93(15) . . ?
F2B B1 F4B 114.7(13) . . ?
F2B B1 F4A 127.3(6) . . ?
F4B B1 F4A 32.8(13) . . ?
F2B B1 F2A 31.2(13) . . ?
F4B B1 F2A 125.5(5) . . ?
F4A B1 F2A 117.7(4) . . ?
F2B B1 F1 119.4(6) . . ?
F4B B1 F1 121.1(5) . . ?
F4A B1 F1 112.5(3) . . ?
F2A B1 F1 112.7(3) . . ?
F2B B1 F3A 75.4(15) . . ?
F4B B1 F3A 69.4(15) . . ?
F4A B1 F3A 102.2(4) . . ?
F2A B1 F3A 106.6(4) . . ?
F1 B1 F3A 103.2(3) . . ?
F2B B1 F3B 98.0(15) . . ?
F4B B1 F3B 102.4(15) . . ?
F4A B1 F3B 70.8(6) . . ?
F2A B1 F3B 67.4(6) . . ?
F1 B1 F3B 91.7(6) . . ?
F3A B1 F3B 165.1(6) . . ?
F2B F2A B1 67.6(12) . . ?
F2B F2A F3B 128.6(14) . . ?
B1 F2A F3B 62.2(5) . . ?
F2A F2B B1 81.2(9) . . ?
F2A F2B F3A 138.5(12) . . ?
B1 F2B F3A 57.5(11) . . ?
B1 F3A F4B 50.7(5) . . ?
B1 F3A F2B 47.1(5) . . ?
F4B F3A F2B 83.4(6) . . ?
B1 F3B F2A 50.4(4) . . ?
B1 F3B F4A 48.7(4) . . ?
F2A F3B F4A 88.4(6) . . ?
F4B F4A B1 71.1(13) . . ?
F4B F4A F3B 129.0(15) . . ?
B1 F4A F3B 60.5(5) . . ?
F4A F4B B1 76.1(8) . . ?
F4A F4B F3A 135.9(13) . . ?
B1 F4B F3A 59.9(11) . . ?

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 N2 1.0(3) . . . . ?
N1 C2 C3 C3 -178.42(18) . . . 7_656 ?
N2 C4 C5 C6 178.41(17) . . . . ?
C9 C4 C5 C6 -0.7(3) . . . . ?
C4 C5 C6 C7 -0.1(3) . . . . ?
C5 C6 C7 C8 0.7(3) . . . . ?
C6 C7 C8 C9 -0.4(3) . . . . ?
C7 C8 C9 N1 -179.37(18) . . . . ?
C7 C8 C9 C4 -0.4(3) . . . . ?
N2 C4 C9 N1 0.9(3) . . . . ?
C5 C4 C9 N1 179.99(16) . . . . ?
N2 C4 C9 C8 -178.16(16) . . . . ?
C5 C4 C9 C8 0.9(3) . . . . ?
C3 C2 N1 C9 0.1(3) . . . . ?
C3 C2 N1 C1 177.87(17) . . . . ?
C8 C9 N1 C2 178.05(17) . . . . ?
C4 C9 N1 C2 -1.0(2) . . . . ?
C8 C9 N1 C1 0.3(3) . . . . ?
C4 C9 N1 C1 -178.74(17) . . . . ?
C2 C3 N2 C4 -1.1(3) . . . . ?
C3 C3 N2 C4 178.34(18) 7_656 . . . ?
C5 C4 N2 C3 -178.96(17) . . . . ?
C9 C4 N2 C3 0.1(3) . . . . ?
F4B B1 F2A F2B -79(2) . . . . ?
F4A B1 F2A F2B -116.9(13) . . . . ?
F1 B1 F2A F2B 109.6(12) . . . . ?
F3A B1 F2A F2B -3.0(13) . . . . ?
F3B B1 F2A F2B -168.5(14) . . . . ?
F2B B1 F2A F3B 168.5(14) . . . . ?
F4B B1 F2A F3B 89(2) . . . . ?
F4A B1 F2A F3B 51.6(7) . . . . ?
F1 B1 F2A F3B -81.9(6) . . . . ?
F3A B1 F2A F3B 165.5(6) . . . . ?
F3B F2A F2B B1 -13.0(16) . . . . ?
B1 F2A F2B F3A 3.7(16) . . . . ?
F3B F2A F2B F3A -9(3) . . . . ?
F4B B1 F2B F2A 118.3(19) . . . . ?
F4A B1 F2B F2A 82.6(19) . . . . ?
F1 B1 F2B F2A -85.8(13) . . . . ?
F3A B1 F2B F2A 177.1(13) . . . . ?
F3B B1 F2B F2A 10.7(13) . . . . ?
F4B B1 F2B F3A -58.7(15) . . . . ?
F4A B1 F2B F3A -94.4(13) . . . . ?
F2A B1 F2B F3A -177.1(13) . . . . ?
F1 B1 F2B F3A 97.2(9) . . . . ?
F3B B1 F2B F3A -166.3(6) . . . . ?
F2B B1 F3A F4B -124.0(7) . . . . ?
F4A B1 F3A F4B 1.7(6) . . . . ?
F2A B1 F3A F4B -122.4(6) . . . . ?
F1 B1 F3A F4B 118.6(5) . . . . ?
F3B B1 F3A F4B -59(2) . . . . ?
F4B B1 F3A F2B 124.0(7) . . . . ?
F4A B1 F3A F2B 125.7(6) . . . . ?
F2A B1 F3A F2B 1.6(7) . . . . ?
F1 B1 F3A F2B -117.4(5) . . . . ?
F3B B1 F3A F2B 65(2) . . . . ?
F2A F2B F3A B1 -4.4(19) . . . . ?
F2A F2B F3A F4B 36(2) . . . . ?
B1 F2B F3A F4B 40.2(6) . . . . ?
F2B B1 F3B F2A -6.0(8) . . . . ?
F4B B1 F3B F2A -123.6(7) . . . . ?
F4A B1 F3B F2A -132.8(6) . . . . ?
F1 B1 F3B F2A 114.0(4) . . . . ?
F3A B1 F3B F2A -69(2) . . . . ?
F2B B1 F3B F4A 126.8(7) . . . . ?
F4B B1 F3B F4A 9.2(8) . . . . ?
F2A B1 F3B F4A 132.8(6) . . . . ?
F1 B1 F3B F4A -113.3(4) . . . . ?
F3A B1 F3B F4A 64(3) . . . . ?
F2B F2A F3B B1 13.6(17) . . . . ?
F2B F2A F3B F4A -19.8(19) . . . . ?
B1 F2A F3B F4A -33.5(4) . . . . ?
F2B B1 F4A F4B 78(2) . . . . ?
F2A B1 F4A F4B 113.4(11) . . . . ?
F1 B1 F4A F4B -113.0(10) . . . . ?
F3A B1 F4A F4B -3.0(11) . . . . ?
F3B B1 F4A F4B 163.3(13) . . . . ?
F2B B1 F4A F3B -85.4(19) . . . . ?
F4B B1 F4A F3B -163.3(13) . . . . ?
F2A B1 F4A F3B -50.0(7) . . . . ?
F1 B1 F4A F3B 83.6(7) . . . . ?
F3A B1 F4A F3B -166.3(7) . . . . ?
B1 F3B F4A F4B -20.4(16) . . . . ?
F2A F3B F4A F4B 14.1(18) . . . . ?
F2A F3B F4A B1 34.5(4) . . . . ?
F3B F4A F4B B1 18.7(14) . . . . ?
B1 F4A F4B F3A 3.9(14) . . . . ?
F3B F4A F4B F3A 23(3) . . . . ?
F2B B1 F4B F4A -121.1(18) . . . . ?
F2A B1 F4B F4A -87.0(16) . . . . ?
F1 B1 F4B F4A 83.5(13) . . . . ?
F3A B1 F4B F4A 176.9(11) . . . . ?
F3B B1 F4B F4A -16.1(12) . . . . ?
F2B B1 F4B F3A 62.1(15) . . . . ?
F4A B1 F4B F3A -176.9(11) . . . . ?
F2A B1 F4B F3A 96.1(12) . . . . ?
F1 B1 F4B F3A -93.4(10) . . . . ?
F3B B1 F4B F3A 167.0(7) . . . . ?
B1 F3A F4B F4A -4.4(16) . . . . ?
F2B F3A F4B F4A -42.0(19) . . . . ?
F2B F3A F4B B1 -37.7(5) . . . . ?


# END of CIF
_chemical_name_common            Methylbiquinoxen
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile/diethylether'
####################################################################### 
# 
# 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 1511789'
_audit_update_record             
;
2016-10-26 deposited with the CCDC.
2017-03-15 downloaded from the CCDC.
;

_audit_creation_date             2015-07-23T11:03:59-00:00
_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,N'-dibenzyl-3,3'-biquinoxalinium bis(tetrafluoroborate), bis (acetonitrile) "
_chemical_formula_moiety         'C30 H24 N4, 2(B F4), 2(C2 H3 N)'
_chemical_formula_sum            'C34 H30 B2 F8 N6'
_chemical_formula_weight         696.26
_chemical_compound_source        'synthesis as described'

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
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                   8.6630(10)
_cell_length_b                   8.7810(10)
_cell_length_c                   22.282(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.376(6)
_cell_angle_gamma                90
_cell_volume                     1687.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    5074
_cell_measurement_theta_min      1.84
_cell_measurement_theta_max      27.63
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.341
_exptl_crystal_size_mid          0.316
_exptl_crystal_size_min          0.309
_exptl_crystal_density_diffrn    1.37
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             716
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.113
_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    '0.5 mm, multiple pinhole'
_diffrn_ambient_temperature      291
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_details      
; 130 frames, detector distance = 115 mm
;

_diffrn_reflns_number            7569
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.452
_diffrn_reflns_theta_max         27.389
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.975
_reflns_number_total             3732
_reflns_number_gt                2296
_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)+(0.1239P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3732
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0595
_refine_ls_wR_factor_ref         0.1985
_refine_ls_wR_factor_gt          0.1801
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.035

#----------------------------------------------------------------------------#
#                   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'
B B 0.0013 0.0007 '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'

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 0.1904(3) 0.0956(2) 0.42629(9) 0.0624(5) Uani 1 d . .
C2 C 0.0701(2) 0.3153(2) 0.46873(9) 0.0596(5) Uani 1 d . .
C3 C 0.0665(2) 0.4710(2) 0.48484(8) 0.0580(5) Uani 1 d . .
C4 C 0.2984(2) 0.5112(2) 0.44704(9) 0.0573(5) Uani 1 d . .
C5 C 0.4197(2) 0.6116(3) 0.43573(10) 0.0642(5) Uani 1 d . .
C6 C 0.5487(3) 0.5564(3) 0.41276(10) 0.0677(5) Uani 1 d . .
C7 C 0.5635(3) 0.4016(3) 0.40113(10) 0.0692(5) Uani 1 d . .
C8 C 0.4481(2) 0.3005(3) 0.41093(9) 0.0636(5) Uani 1 d . .
C9 C 0.3132(2) 0.3546(2) 0.43300(8) 0.0558(4) Uani 1 d . .
C10 C 0.1804(2) 0.0742(2) 0.35921(9) 0.0590(5) Uani 1 d . .
C11 C 0.0587(3) 0.1328(3) 0.32226(11) 0.0743(6) Uani 1 d . .
C12 C 0.0545(4) 0.1098(4) 0.26039(13) 0.0956(9) Uani 1 d . .
C13 C 0.1682(5) 0.0302(4) 0.23625(14) 0.0977(9) Uani 1 d . .
C14 C 0.2869(4) -0.0298(4) 0.27247(14) 0.0922(8) Uani 1 d . .
C15 C 0.2942(3) -0.0094(3) 0.33389(12) 0.0730(6) Uani 1 d . .
C16 C -0.0929(6) 0.7197(5) 0.2745(2) 0.1324(13) Uani 1 d . .
H16A H 0.0106 0.7443 0.2657 0.199 Uiso 1 calc . .
H16B H -0.1386 0.8067 0.292 0.199 Uiso 1 calc . .
H16C H -0.1538 0.6919 0.2379 0.199 Uiso 1 calc . .
C17 C -0.0882(4) 0.5933(4) 0.31648(16) 0.0990(9) Uani 1 d . .
B1 B 0.2678(3) 0.0351(3) 0.58750(13) 0.0706(6) Uani 1 d . .
N1 N 0.18934(18) 0.26080(17) 0.44359(7) 0.0558(4) Uani 1 d . .
N2 N 0.17509(19) 0.56668(18) 0.47335(7) 0.0593(4) Uani 1 d . .
N3 N -0.0844(4) 0.4945(4) 0.34867(18) 0.1267(10) Uani 1 d . .
F1 F 0.3129(3) 0.0245(5) 0.64574(10) 0.1815(14) Uani 1 d . .
F2 F 0.1542(3) 0.1412(3) 0.57736(11) 0.1334(8) Uani 1 d . .
F3 F 0.2062(3) -0.0968(2) 0.56658(18) 0.1703(12) Uani 1 d . .
F4 F 0.39185(19) 0.0683(2) 0.55640(8) 0.1006(5) Uani 1 d . .
H1A H 0.285(3) 0.056(3) 0.4459(11) 0.069(6) Uiso 1 d . .
H1B H 0.099(3) 0.059(3) 0.4406(12) 0.075(7) Uiso 1 d . .
H2 H -0.009(3) 0.249(3) 0.4755(12) 0.075(7) Uiso 1 d . .
H5 H 0.406(3) 0.711(3) 0.4459(10) 0.065(6) Uiso 1 d . .
H6 H 0.634(3) 0.626(3) 0.4064(12) 0.085(7) Uiso 1 d . .
H7 H 0.663(4) 0.365(3) 0.3857(13) 0.094(8) Uiso 1 d . .
H8 H 0.461(3) 0.198(3) 0.4052(11) 0.073(6) Uiso 1 d . .
H11 H -0.017(3) 0.195(3) 0.3414(12) 0.087(8) Uiso 1 d . .
H12 H -0.025(4) 0.161(4) 0.2377(15) 0.106(9) Uiso 1 d . .
H13 H 0.178(4) 0.026(4) 0.1963(17) 0.105(10) Uiso 1 d . .
H14 H 0.371(4) -0.101(4) 0.2545(16) 0.120(11) Uiso 1 d . .
H15 H 0.385(3) -0.048(3) 0.3598(13) 0.080(7) 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 C10 1.501(3) . ?
C1 N1 1.501(2) . ?
C2 N1 1.311(3) . ?
C2 C3 1.415(3) . ?
C3 N2 1.304(3) . ?
C3 C3 1.479(4) 3_566 ?
C4 N2 1.356(3) . ?
C4 C5 1.413(3) . ?
C4 C9 1.418(3) . ?
C5 C6 1.361(3) . ?
C6 C7 1.392(3) . ?
C7 C8 1.370(3) . ?
C8 C9 1.393(3) . ?
C9 N1 1.390(3) . ?
C10 C11 1.375(3) . ?
C10 C15 1.390(3) . ?
C11 C12 1.390(4) . ?
C12 C13 1.360(5) . ?
C13 C14 1.353(5) . ?
C14 C15 1.376(4) . ?
C16 C17 1.450(5) . ?
C17 N3 1.124(4) . ?
B1 F1 1.323(3) . ?
B1 F3 1.341(3) . ?
B1 F2 1.358(3) . ?
B1 F4 1.364(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
C10 C1 N1 112.06(16) . . ?
N1 C2 C3 119.91(19) . . ?
N2 C3 C2 122.61(19) . . ?
N2 C3 C3 118.3(2) . 3_566 ?
C2 C3 C3 119.0(2) . 3_566 ?
N2 C4 C5 118.82(18) . . ?
N2 C4 C9 122.32(17) . . ?
C5 C4 C9 118.80(19) . . ?
C6 C5 C4 119.7(2) . . ?
C5 C6 C7 120.8(2) . . ?
C8 C7 C6 121.4(2) . . ?
C7 C8 C9 119.0(2) . . ?
N1 C9 C8 122.98(18) . . ?
N1 C9 C4 116.73(17) . . ?
C8 C9 C4 120.28(18) . . ?
C11 C10 C15 119.2(2) . . ?
C11 C10 C1 121.2(2) . . ?
C15 C10 C1 119.56(19) . . ?
C10 C11 C12 119.1(3) . . ?
C13 C12 C11 120.9(3) . . ?
C14 C13 C12 120.2(3) . . ?
C13 C14 C15 120.3(3) . . ?
C14 C15 C10 120.3(3) . . ?
N3 C17 C16 179.4(4) . . ?
F1 B1 F3 110.6(3) . . ?
F1 B1 F2 110.8(3) . . ?
F3 B1 F2 106.1(2) . . ?
F1 B1 F4 109.8(2) . . ?
F3 B1 F4 108.3(3) . . ?
F2 B1 F4 111.2(2) . . ?
C2 N1 C9 120.51(16) . . ?
C2 N1 C1 119.12(17) . . ?
C9 N1 C1 120.37(17) . . ?
C3 N2 C4 117.72(17) . . ?

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 N2 3.1(3) . . . . ?
N1 C2 C3 C3 -177.8(2) . . . 3_566 ?
N2 C4 C5 C6 176.01(18) . . . . ?
C9 C4 C5 C6 -1.2(3) . . . . ?
C4 C5 C6 C7 -1.0(3) . . . . ?
C5 C6 C7 C8 1.6(3) . . . . ?
C6 C7 C8 C9 0.0(3) . . . . ?
C7 C8 C9 N1 179.19(17) . . . . ?
C7 C8 C9 C4 -2.2(3) . . . . ?
N2 C4 C9 N1 4.4(3) . . . . ?
C5 C4 C9 N1 -178.52(16) . . . . ?
N2 C4 C9 C8 -174.30(17) . . . . ?
C5 C4 C9 C8 2.8(3) . . . . ?
N1 C1 C10 C11 -57.5(3) . . . . ?
N1 C1 C10 C15 124.0(2) . . . . ?
C15 C10 C11 C12 -1.4(3) . . . . ?
C1 C10 C11 C12 -179.9(2) . . . . ?
C10 C11 C12 C13 0.2(4) . . . . ?
C11 C12 C13 C14 0.8(5) . . . . ?
C12 C13 C14 C15 -0.6(5) . . . . ?
C13 C14 C15 C10 -0.6(4) . . . . ?
C11 C10 C15 C14 1.6(4) . . . . ?
C1 C10 C15 C14 -179.8(2) . . . . ?
C3 C2 N1 C9 0.5(3) . . . . ?
C3 C2 N1 C1 -179.43(17) . . . . ?
C8 C9 N1 C2 174.70(18) . . . . ?
C4 C9 N1 C2 -4.0(2) . . . . ?
C8 C9 N1 C1 -5.3(3) . . . . ?
C4 C9 N1 C1 175.98(16) . . . . ?
C10 C1 N1 C2 112.9(2) . . . . ?
C10 C1 N1 C9 -67.1(2) . . . . ?
C2 C3 N2 C4 -2.6(3) . . . . ?
C3 C3 N2 C4 178.2(2) 3_566 . . . ?
C5 C4 N2 C3 -178.20(17) . . . . ?
C9 C4 N2 C3 -1.1(3) . . . . ?


# END of CIF
_chemical_name_common            
'Benzylbiquinoxen bis (tetrafluoroborate), bis (acetonitrile)'
####################################################################### 
# 
# 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 1511788'
_audit_update_record             
;
2016-10-26 deposited with the CCDC.
2017-03-15 downloaded from the CCDC.
;

_audit_creation_date             2015-07-14T16:06:18-00:00
_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,N'-diethyl-3,3'-biquinoxalinium bis(tetrafluoroborate)"
_chemical_formula_moiety         'C20 H20 N4, 2(B F4)'
_chemical_formula_sum            'C20 H20 B2 F8 N4'
_chemical_formula_weight         490.02
_chemical_compound_source        'synthesis as described'

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
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'
'-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                   9.371(4)
_cell_length_b                   14.361(7)
_cell_length_c                   15.685(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.28(3)
_cell_angle_gamma                90
_cell_volume                     2069.9(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    7452
_cell_measurement_theta_min      1.32
_cell_measurement_theta_max      25.63
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.319
_exptl_crystal_size_mid          0.193
_exptl_crystal_size_min          0.127
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1000
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.144
_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    '0.5 mm, multiple pinhole'
_diffrn_ambient_temperature      180
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_details      
; 239 frames, detector distance = 130 mm
;
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_number            7293
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.631
_diffrn_reflns_theta_max         25.624
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.981
_reflns_number_total             1932
_reflns_number_gt                1621
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   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)+(0.0481P)²+1.8430P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1932
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.1082
_refine_ls_wR_factor_gt          0.0981
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.04

#----------------------------------------------------------------------------#
#                   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 0.55236(17) 0.16528(12) 0.62468(11) 0.0328(4) Uani 1 d . .
H1A H 0.51 0.2011 0.5736 0.039 Uiso 1 calc . .
H1B H 0.5405 0.2005 0.6756 0.039 Uiso 1 calc . .
C2 C 0.80092(18) 0.15189(11) 0.70232(11) 0.0296(4) Uani 1 d . .
H2 H 0.7652 0.162 0.7528 0.035 Uiso 1 calc . .
C3 C 0.95132(18) 0.13789(11) 0.70713(10) 0.0290(4) Uani 1 d . .
C4 C 0.91591(17) 0.12395(10) 0.55923(11) 0.0289(4) Uani 1 d . .
C5 C 0.97405(18) 0.11084(11) 0.48364(11) 0.0331(4) Uani 1 d . .
H5 H 1.0739 0.1039 0.4881 0.04 Uiso 1 calc . .
C6 C 0.8838(2) 0.10833(12) 0.40379(11) 0.0357(4) Uani 1 d . .
H6 H 0.9223 0.0989 0.3541 0.043 Uiso 1 calc . .
C7 C 0.7324(2) 0.11998(11) 0.39664(11) 0.0347(4) Uani 1 d . .
H7 H 0.6723 0.1182 0.3419 0.042 Uiso 1 calc . .
C8 C 0.67166(19) 0.13384(11) 0.46837(11) 0.0322(4) Uani 1 d . .
H8 H 0.5718 0.1419 0.4626 0.039 Uiso 1 calc . .
C9 C 0.76298(18) 0.13562(10) 0.55066(10) 0.0282(4) Uani 1 d . .
C10 C 0.4736(2) 0.07333(13) 0.62338(12) 0.0395(4) Uani 1 d . .
H1C H 0.517 0.0372 0.6732 0.059 Uiso 1 calc . .
H10A H 0.4807 0.0399 0.5714 0.059 Uiso 1 calc . .
H10C H 0.3731 0.0844 0.6247 0.059 Uiso 1 calc . .
N1 N 0.71083(14) 0.15069(9) 0.62623(9) 0.0278(3) Uani 1 d . .
N2 N 1.00831(15) 0.12515(9) 0.63778(9) 0.0300(3) Uani 1 d . .
F1 F 0.79286(16) -0.05521(9) 0.67962(13) 0.0853(5) Uani 1 d . .
F2 F 0.83257(12) -0.20771(8) 0.68094(9) 0.0570(4) Uani 1 d . .
F3 F 0.60885(11) -0.15437(9) 0.68635(7) 0.0489(3) Uani 1 d . .
F4 F 0.69381(15) -0.13911(15) 0.56322(8) 0.0890(6) Uani 1 d . .
B1 B 0.7321(2) -0.13973(14) 0.65200(13) 0.0350(4) 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 1.495(2) . ?
C1 C10 1.511(2) . ?
C2 N1 1.320(2) . ?
C2 C3 1.411(2) . ?
C3 N2 1.315(2) . ?
C3 C3 1.470(3) 2_756 ?
C4 N2 1.360(2) . ?
C4 C5 1.411(2) . ?
C4 C9 1.423(2) . ?
C5 C6 1.368(3) . ?
C6 C7 1.411(3) . ?
C7 C8 1.371(2) . ?
C8 C9 1.402(2) . ?
C9 N1 1.385(2) . ?
F1 B1 1.374(3) . ?
F2 B1 1.370(2) . ?
F3 B1 1.383(2) . ?
F4 B1 1.368(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
N1 C1 C10 111.02(14) . . ?
N1 C2 C3 120.12(15) . . ?
N2 C3 C2 122.59(16) . . ?
N2 C3 C3 118.49(18) . 2_756 ?
C2 C3 C3 118.91(18) . 2_756 ?
N2 C4 C5 118.73(15) . . ?
N2 C4 C9 122.33(15) . . ?
C5 C4 C9 118.93(15) . . ?
C6 C5 C4 120.12(16) . . ?
C5 C6 C7 120.10(16) . . ?
C8 C7 C6 121.62(16) . . ?
C7 C8 C9 118.78(16) . . ?
N1 C9 C8 122.46(15) . . ?
N1 C9 C4 117.08(15) . . ?
C8 C9 C4 120.44(15) . . ?
C2 N1 C9 120.36(14) . . ?
C2 N1 C1 118.06(14) . . ?
C9 N1 C1 121.58(14) . . ?
C3 N2 C4 117.48(14) . . ?
F4 B1 F2 111.61(17) . . ?
F4 B1 F1 108.97(18) . . ?
F2 B1 F1 108.02(16) . . ?
F4 B1 F3 108.95(16) . . ?
F2 B1 F3 109.55(15) . . ?
F1 B1 F3 109.72(17) . . ?

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 N2 1.4(2) . . . . ?
N1 C2 C3 C3 -178.89(10) . . . 2_756 ?
N2 C4 C5 C6 179.32(15) . . . . ?
C9 C4 C5 C6 -0.8(2) . . . . ?
C4 C5 C6 C7 0.8(2) . . . . ?
C5 C6 C7 C8 -0.1(3) . . . . ?
C6 C7 C8 C9 -0.5(2) . . . . ?
C7 C8 C9 N1 178.95(14) . . . . ?
C7 C8 C9 C4 0.5(2) . . . . ?
N2 C4 C9 N1 1.5(2) . . . . ?
C5 C4 C9 N1 -178.38(13) . . . . ?
N2 C4 C9 C8 -179.95(14) . . . . ?
C5 C4 C9 C8 0.2(2) . . . . ?
C3 C2 N1 C9 0.1(2) . . . . ?
C3 C2 N1 C1 179.61(14) . . . . ?
C8 C9 N1 C2 -179.92(14) . . . . ?
C4 C9 N1 C2 -1.4(2) . . . . ?
C8 C9 N1 C1 0.5(2) . . . . ?
C4 C9 N1 C1 179.07(13) . . . . ?
C10 C1 N1 C2 -95.52(17) . . . . ?
C10 C1 N1 C9 84.02(18) . . . . ?
C2 C3 N2 C4 -1.3(2) . . . . ?
C3 C3 N2 C4 178.99(9) 2_756 . . . ?
C5 C4 N2 C3 179.72(14) . . . . ?
C9 C4 N2 C3 -0.2(2) . . . . ?


# END of CIF
_chemical_name_common            Ethylbiquinoxen
