####################################################################### 
# 
# 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_1_AN-100K
_database_code_depnum_ccdc_archive 'CCDC 1886467'
_audit_update_record             
;
2018-12-20 deposited with the CCDC.
2018-12-21 downloaded from the CCDC.
;

_publ_section_title              
;
?
;

_publ_requested_journal          
;
J. Phys. Chem. C
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6


# SUBMISSION DETAILS 
_publ_contact_author_name        'Yasukazu HIRAO'
_publ_contact_author_address     
;
Department of Chemistry, Graduate School of Science, Osaka University, 
Machikaneyama 1-1, Toyonaka, Osaka 560-0043 (Japan)
;
_publ_contact_author_email       y-hirao@chem.sci.osaka-u.ac.jp
_publ_contact_author_fax         +81-6-6850-5387
_publ_contact_author_phone       +81-6-6850-5385

loop_
_publ_author_name
_publ_author_address
'Inokuchi, Daisuke'
;
Department of Chemistry, Graduate School of Science, Osaka University, 
Machikaneyama 1-1, Toyonaka, Osaka, 560-0043, Japan
;
'Hirao, Yasukazu'
;
Department of Chemistry, Graduate School of Science, Osaka University, 
Machikaneyama 1-1, Toyonaka, Osaka, 560-0043, Japan
;
'Takahashi, Kazuyuki'
;
Department of Chemistry, Graduate School of Science, Kobe University, 
Nada, Hyogo, 657-8501, Japan
;
'Matsumoto, Kouzou'
;
Institute of Natural Sciences, Senshu University, 
Kawasaki, Kanagawa, 214-8580, Japan
;
'Kubo, Takashi'
;
Department of Chemistry, Graduate School of Science, Osaka University, 
Machikaneyama 1-1, Toyonaka, Osaka, 560-0043, Japan
;

_chemical_name_systematic        
'bis(4-Pyridyl)bis(pyridinium-4-yl)methane bis(tetrafluoroborate) acetonitrile solvate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H18 N4 2+, (B1 F4 1-)2, C2H3N1'
_chemical_formula_sum            'C23 H21 B2 F8 N5'
_chemical_formula_weight         541.07

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      hexagonal
_space_group_IT_number           178
_space_group_name_H-M_alt        'P 61 2 2'
_space_group_name_Hall           'P 61 2 (0 0 -1)'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'x-y, x, z+1/6'
'y, -x+y, z+5/6'
'x-y, -y, -z'
'-x, -x+y, -z+2/3'
'y, x, -z+1/3'
'-y, -x, -z+5/6'
'x, x-y, -z+1/6'
'-x+y, y, -z+1/2'

_cell_length_a                   10.6131(2)
_cell_length_b                   10.6131(2)
_cell_length_c                   37.846(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3691.8(3)
_cell_formula_units_Z            6
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    35110
_cell_measurement_theta_min      3.51
_cell_measurement_theta_max      68.24

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_F_000             1656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.140
_shelx_estimated_absorpt_T_min   0.600
_shelx_estimated_absorpt_T_max   0.804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7316
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
Empirical Absorption Correction   March 2001 T. Higashi
    Rigaku Corporation, Tokyo, Japan
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus rotating anode'
_diffrn_measurement_device_type  
;
Rigaku VariMax RAPID FR-E
;
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            46220
_diffrn_reflns_av_unetI/netI     0.0120
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_theta_min         4.811
_diffrn_reflns_theta_max         68.239
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2266
_reflns_number_gt                2212
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.567
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    Sir2004
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    
;
Yadokari-XG 2009 (K. Wakita, T. Nemoto, et al., 2009)
;
_computing_publication_material  
;
Yadokari-XG 2009 (K. Wakita, T. Nemoto, et al., 2009)
;
_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)+(0.1108P)²+4.6658P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 783 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(3)
_chemical_absolute_configuration .
_refine_ls_number_reflns         2266
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0669
_refine_ls_wR_factor_ref         0.1951
_refine_ls_wR_factor_gt          0.1944
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.117
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N -0.0126(4) 0.2881(4) 0.11470(9) 0.0278(8) Uani 1 1 d . . . . .
H12 H -0.095463 0.266523 0.104476 0.033 Uiso 1 1 calc R U . . .
N2 N 0.7422(4) 0.5338(4) 0.09136(10) 0.0303(9) Uani 1 1 d . . . . .
N3 N 0.7641(13) 0.8821(6) 0.083333 0.153(9) Uani 1 2 d S T P . .
C1 C 0.3851(5) 0.3851(5) 0.166667 0.0194(11) Uani 1 2 d S T P . .
C2 C 0.2445(4) 0.3555(4) 0.14779(10) 0.0200(8) Uani 1 1 d . . . . .
C3 C 0.1927(5) 0.4525(4) 0.14757(10) 0.0224(9) Uani 1 1 d . . . . .
H1 H 0.245955 0.543782 0.159134 0.027 Uiso 1 1 calc R U . . .
C4 C 0.0645(5) 0.4165(5) 0.13062(11) 0.0249(9) Uani 1 1 d . . . . .
H2 H 0.030405 0.483981 0.130255 0.030 Uiso 1 1 calc R U . . .
C5 C 0.0332(5) 0.1908(5) 0.11389(12) 0.0322(10) Uani 1 1 d . . . . .
H3 H -0.023637 0.100070 0.102314 0.039 Uiso 1 1 calc R U . . .
C6 C 0.1620(5) 0.2226(5) 0.12977(11) 0.0250(9) Uani 1 1 d . . . . .
H4 H 0.195594 0.154882 0.128621 0.030 Uiso 1 1 calc R U . . .
C7 C 0.5090(5) 0.4327(4) 0.13924(11) 0.0225(9) Uani 1 1 d . . . . .
C8 C 0.6529(5) 0.4983(5) 0.15067(12) 0.0287(9) Uani 1 1 d . . . . .
H5 H 0.674276 0.510432 0.175223 0.034 Uiso 1 1 calc R U . . .
C9 C 0.7646(5) 0.5458(5) 0.12632(12) 0.0297(10) Uani 1 1 d . . . . .
H6 H 0.861691 0.588949 0.134776 0.036 Uiso 1 1 calc R U . . .
C10 C 0.6046(5) 0.4700(5) 0.08009(12) 0.0304(10) Uani 1 1 d . . . . .
H7 H 0.586686 0.459829 0.055373 0.036 Uiso 1 1 calc R U . . .
C11 C 0.4860(5) 0.4178(5) 0.10299(11) 0.0256(9) Uani 1 1 d . . . . .
H8 H 0.389771 0.372128 0.093824 0.031 Uiso 1 1 calc R U . . .
C12 C 0.4740(10) 0.7370(5) 0.083333 0.055(2) Uani 1 2 d S T P . .
H9 H 0.438419 0.666800 0.063840 0.082 Uiso 0.5 1 calc R U P . .
H10 H 0.438419 0.805616 0.080352 0.082 Uiso 0.5 1 calc R U P . .
H11 H 0.438419 0.685213 0.105808 0.082 Uiso 0.5 1 calc R U P . .
C13 C 0.630(3) 0.8148(15) 0.083333 0.134(8) Uani 1 2 d S T P . .
F1 F 0.2268(5) 0.2818(4) 0.03412(8) 0.0557(10) Uani 1 1 d . . . . .
F2 F 0.1827(5) 0.4499(4) 0.05843(9) 0.0640(12) Uani 1 1 d . . . . .
F3 F 0.1373(8) 0.3975(7) 0.00166(11) 0.107(2) Uani 1 1 d . . . . .
F4 F 0.3608(7) 0.5123(5) 0.01847(16) 0.117(2) Uani 1 1 d . . . . .
B1 B 0.2214(8) 0.4057(7) 0.02827(14) 0.0400(14) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C4 1.332(6) . ?
N1 C5 1.343(6) . ?
N1 H12 0.8800 . ?
N2 C10 1.336(6) . ?
N2 C9 1.339(6) . ?
N3 C13 1.24(3) . ?
C1 C2 1.539(5) 9 ?
C1 C2 1.539(5) . ?
C1 C7 1.548(5) . ?
C1 C7 1.549(5) 9 ?
C2 C3 1.388(6) . ?
C2 C6 1.409(6) . ?
C3 C4 1.375(6) . ?
C3 H1 0.9500 . ?
C4 H2 0.9500 . ?
C5 C6 1.372(6) . ?
C5 H3 0.9500 . ?
C6 H4 0.9500 . ?
C7 C11 1.389(6) . ?
C7 C8 1.393(6) . ?
C8 C9 1.382(6) . ?
C8 H5 0.9500 . ?
C9 H6 0.9500 . ?
C10 C11 1.395(6) . ?
C10 H7 0.9500 . ?
C11 H8 0.9500 . ?
C12 C13 1.43(3) . ?
C12 H9 0.9800 . ?
C12 H10 0.9800 . ?
C12 H11 0.9800 . ?
C12 H9 0.98(13) 11_565 ?
C12 H10 0.98(4) 11_565 ?
C12 H11 0.98(10) 11_565 ?
F1 B1 1.363(6) . ?
F2 B1 1.373(6) . ?
F3 B1 1.319(8) . ?
F4 B1 1.391(8) . ?

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
C4 N1 C5 121.6(4) . . ?
C4 N1 H12 119.2 . . ?
C5 N1 H12 119.2 . . ?
C10 N2 C9 117.4(4) . . ?
C2 C1 C2 108.1(4) 9 . ?
C2 C1 C7 110.9(2) 9 . ?
C2 C1 C7 109.5(2) . . ?
C2 C1 C7 109.5(2) 9 9 ?
C2 C1 C7 110.9(2) . 9 ?
C7 C1 C7 108.0(4) . 9 ?
C3 C2 C6 117.4(4) . . ?
C3 C2 C1 123.7(3) . . ?
C6 C2 C1 118.9(3) . . ?
C4 C3 C2 120.1(4) . . ?
C4 C3 H1 120.0 . . ?
C2 C3 H1 120.0 . . ?
N1 C4 C3 120.7(4) . . ?
N1 C4 H2 119.6 . . ?
C3 C4 H2 119.6 . . ?
N1 C5 C6 120.0(4) . . ?
N1 C5 H3 120.0 . . ?
C6 C5 H3 120.0 . . ?
C5 C6 C2 120.1(4) . . ?
C5 C6 H4 119.9 . . ?
C2 C6 H4 119.9 . . ?
C11 C7 C8 116.8(4) . . ?
C11 C7 C1 123.5(4) . . ?
C8 C7 C1 119.7(3) . . ?
C9 C8 C7 120.1(4) . . ?
C9 C8 H5 120.0 . . ?
C7 C8 H5 120.0 . . ?
N2 C9 C8 123.0(4) . . ?
N2 C9 H6 118.5 . . ?
C8 C9 H6 118.5 . . ?
N2 C10 C11 123.0(4) . . ?
N2 C10 H7 118.5 . . ?
C11 C10 H7 118.5 . . ?
C7 C11 C10 119.7(4) . . ?
C7 C11 H8 120.1 . . ?
C10 C11 H8 120.1 . . ?
C13 C12 H9 109.5 . . ?
C13 C12 H10 109.5 . . ?
H9 C12 H10 109.5 . . ?
C13 C12 H11 109.5 . . ?
H9 C12 H11 109.5 . . ?
H10 C12 H11 109.5 . . ?
C13 C12 H9 109(3) . 11_565 ?
H9 C12 H9 141.1 . 11_565 ?
H10 C12 H9 56.3 . 11_565 ?
H11 C12 H9 56.2 . 11_565 ?
C13 C12 H10 109.5(7) . 11_565 ?
H9 C12 H10 56.3 . 11_565 ?
H10 C12 H10 141.1 . 11_565 ?
H11 C12 H10 56.3 . 11_565 ?
H9 C12 H10 109.5 11_565 11_565 ?
C13 C12 H11 109(2) . 11_565 ?
H9 C12 H11 56.3 . 11_565 ?
H10 C12 H11 56.3 . 11_565 ?
H11 C12 H11 141.1 . 11_565 ?
H9 C12 H11 109.5 11_565 11_565 ?
H10 C12 H11 109.5 11_565 11_565 ?
N3 C13 C12 180.0 . . ?
F3 B1 F1 114.5(6) . . ?
F3 B1 F2 110.5(5) . . ?
F1 B1 F2 111.0(4) . . ?
F3 B1 F4 105.0(6) . . ?
F1 B1 F4 106.7(5) . . ?
F2 B1 F4 108.8(5) . . ?

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
C2 C1 C2 C3 137.7(4) 9 . . . ?
C7 C1 C2 C3 -101.4(4) . . . . ?
C7 C1 C2 C3 17.7(5) 9 . . . ?
C2 C1 C2 C6 -41.9(3) 9 . . . ?
C7 C1 C2 C6 79.0(5) . . . . ?
C7 C1 C2 C6 -161.9(4) 9 . . . ?
C6 C2 C3 C4 0.9(6) . . . . ?
C1 C2 C3 C4 -178.7(3) . . . . ?
C5 N1 C4 C3 -1.5(6) . . . . ?
C2 C3 C4 N1 1.0(6) . . . . ?
C4 N1 C5 C6 0.2(7) . . . . ?
N1 C5 C6 C2 1.7(7) . . . . ?
C3 C2 C6 C5 -2.2(6) . . . . ?
C1 C2 C6 C5 177.4(4) . . . . ?
C2 C1 C7 C11 105.8(4) 9 . . . ?
C2 C1 C7 C11 -13.4(5) . . . . ?
C7 C1 C7 C11 -134.2(4) 9 . . . ?
C2 C1 C7 C8 -76.1(5) 9 . . . ?
C2 C1 C7 C8 164.7(4) . . . . ?
C7 C1 C7 C8 43.8(3) 9 . . . ?
C11 C7 C8 C9 0.4(6) . . . . ?
C1 C7 C8 C9 -177.8(4) . . . . ?
C10 N2 C9 C8 -1.3(7) . . . . ?
C7 C8 C9 N2 0.9(7) . . . . ?
C9 N2 C10 C11 0.5(6) . . . . ?
C8 C7 C11 C10 -1.2(6) . . . . ?
C1 C7 C11 C10 176.9(4) . . . . ?
N2 C10 C11 C7 0.7(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H12 N2 0.88 1.87 2.741(5) 168.7 11_455

_refine_diff_density_max         0.566
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.077




data_1_AN-200K
_database_code_depnum_ccdc_archive 'CCDC 1886468'
_audit_update_record             
;
2018-12-20 deposited with the CCDC.
2018-12-21 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_SHFSU01_1_AN-200K         
;
PROBLEM: The absolute value of parameter shift to su ratio > 0.20
RESPONSE: The H atoms of the solvated acetonitrile molecules are disordered due to the rotation of the methy group.
;
_vrf_PLAT080_1_AN-200K         
;
PROBLEM: Maximum Shift/Error ............................       0.29 Why ?
RESPONSE: TThe H atoms of the solvated acetonitrile molecules are disordered due to the rotation of the methy group.
;
# Added during the CSD deposition process: Thursday 20 December 2018 06:54 AM
# end Validation Reply Form


_publ_section_title              
;
?
;

_publ_requested_journal          
;
J. Phys. Chem. C
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6


# SUBMISSION DETAILS 
_publ_contact_author_name        'Yasukazu HIRAO'
_publ_contact_author_address     
;
Department of Chemistry, Graduate School of Science, Osaka University, 
Machikaneyama 1-1, Toyonaka, Osaka 560-0043 (Japan)
;
_publ_contact_author_email       y-hirao@chem.sci.osaka-u.ac.jp
_publ_contact_author_fax         +81-6-6850-5387
_publ_contact_author_phone       +81-6-6850-5385

loop_
_publ_author_name
_publ_author_address
'Inokuchi, Daisuke'
;
Department of Chemistry, Graduate School of Science, Osaka University, 
Machikaneyama 1-1, Toyonaka, Osaka, 560-0043, Japan
;
'Hirao, Yasukazu'
;
Department of Chemistry, Graduate School of Science, Osaka University, 
Machikaneyama 1-1, Toyonaka, Osaka, 560-0043, Japan
;
'Takahashi, Kazuyuki'
;
Department of Chemistry, Graduate School of Science, Kobe University, 
Nada, Hyogo, 657-8501, Japan
;
'Matsumoto, Kouzou'
;
Institute of Natural Sciences, Senshu University, 
Kawasaki, Kanagawa, 214-8580, Japan
;
'Kubo, Takashi'
;
Department of Chemistry, Graduate School of Science, Osaka University, 
Machikaneyama 1-1, Toyonaka, Osaka, 560-0043, Japan
;

_chemical_name_systematic        
'bis(4-Pyridyl)bis(pyridinium-4-yl)methane bis(tetrafluoroborate) acetonitrile solvate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H18 N4 2+, (B1 F4 1-)2, C2H3N1'
_chemical_formula_sum            'C23 H21 B2 F8 N5'
_chemical_formula_weight         541.07

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      hexagonal
_space_group_IT_number           178
_space_group_name_H-M_alt        'P 61 2 2'
_space_group_name_Hall           'P 61 2 (0 0 -1)'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'x-y, x, z+1/6'
'y, -x+y, z+5/6'
'x-y, -y, -z'
'-x, -x+y, -z+2/3'
'y, x, -z+1/3'
'-y, -x, -z+5/6'
'x, x-y, -z+1/6'
'-x+y, y, -z+1/2'

_cell_length_a                   10.6229(2)
_cell_length_b                   10.6229(2)
_cell_length_c                   38.184(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3731.7(3)
_cell_formula_units_Z            6
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    43283
_cell_measurement_theta_min      3.47
_cell_measurement_theta_max      68.24

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_F_000             1656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.128
_shelx_estimated_absorpt_T_min   0.602
_shelx_estimated_absorpt_T_max   0.806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7928
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
Empirical Absorption Correction   March 2001 T. Higashi
    Rigaku Corporation, Tokyo, Japan
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus rotating anode'
_diffrn_measurement_device_type  
;
Rigaku VariMax RAPID FR-E
;
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            46478
_diffrn_reflns_av_unetI/netI     0.0101
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_theta_min         4.807
_diffrn_reflns_theta_max         68.234
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2283
_reflns_number_gt                2227
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.568
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    Sir2004
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    
;
Yadokari-XG 2009 (K. Wakita, T. Nemoto, et al., 2009)
;
_computing_publication_material  
;
Yadokari-XG 2009 (K. Wakita, T. Nemoto, et al., 2009)
;
_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)+(0.1307P)²+4.1479P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 777 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(3)
_chemical_absolute_configuration .
_refine_ls_number_reflns         2283
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0763
_refine_ls_wR_factor_ref         0.2205
_refine_ls_wR_factor_gt          0.2198
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.286
_refine_ls_shift/su_mean         0.006

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 1.0002(4) 0.7068(5) 0.11296(10) 0.0392(10) Uani 1 1 d . . . . .
H9 H 1.081991 0.728854 0.102208 0.047 Uiso 1 1 calc R U . . .
N2 N 0.2461(5) 0.4604(5) 0.09361(11) 0.0429(10) Uani 1 1 d . . . . .
N3 N 0.2273(14) 0.1136(7) 0.083333 0.179(10) Uani 1 2 d S T P . .
C1 C 0.6075(5) 0.6075(5) 0.166667 0.0250(12) Uani 1 2 d S T P . .
C2 C 0.7473(5) 0.6382(5) 0.14741(10) 0.0262(9) Uani 1 1 d . . . . .
C3 C 0.7999(5) 0.5429(5) 0.14650(11) 0.0293(9) Uani 1 1 d . . . . .
H1 H 0.748314 0.451711 0.158061 0.035 Uiso 1 1 calc R U . . .
C4 C 0.9272(5) 0.5794(5) 0.12887(11) 0.0340(10) Uani 1 1 d . . . . .
H2 H 0.962348 0.512987 0.128148 0.041 Uiso 1 1 calc R U . . .
C5 C 0.9546(6) 0.8027(6) 0.11266(14) 0.0436(12) Uani 1 1 d . . . . .
H3 H 1.009805 0.893018 0.100911 0.052 Uiso 1 1 calc R U . . .
C6 C 0.8274(5) 0.7713(5) 0.12934(12) 0.0338(10) Uani 1 1 d . . . . .
H4 H 0.793562 0.838822 0.128718 0.041 Uiso 1 1 calc R U . . .
C7 C 0.4813(5) 0.5603(4) 0.13992(11) 0.0274(9) Uani 1 1 d . . . . .
C8 C 0.5024(5) 0.5759(5) 0.10395(11) 0.0349(10) Uani 1 1 d . . . . .
H5 H 0.597664 0.621538 0.094341 0.042 Uiso 1 1 calc R U . . .
C9 C 0.3807(6) 0.5231(6) 0.08215(13) 0.0416(11) Uani 1 1 d . . . . .
H6 H 0.396234 0.533226 0.057557 0.050 Uiso 1 1 calc R U . . .
C10 C 0.2254(6) 0.4471(6) 0.12853(14) 0.0445(12) Uani 1 1 d . . . . .
H7 H 0.128843 0.402196 0.137293 0.053 Uiso 1 1 calc R U . . .
C11 C 0.3378(5) 0.4955(6) 0.15191(13) 0.0384(11) Uani 1 1 d . . . . .
H8 H 0.318405 0.485056 0.176343 0.046 Uiso 1 1 calc R U . . .
C12 C 0.5157(13) 0.2579(6) 0.083333 0.077(3) Uani 1 2 d S T P . .
H10 H 0.551244 0.190442 0.078439 0.115 Uiso 0.5 1 calc R U P . .
H11 H 0.551244 0.302978 0.106303 0.115 Uiso 0.5 1 calc R U P . .
H12 H 0.551244 0.333446 0.065258 0.115 Uiso 0.5 1 calc R U P . .
C13 C 0.365(3) 0.1827(17) 0.083333 0.158(9) Uani 1 2 d S T P . .
F1 F 0.8081(7) 0.5474(6) 0.05664(10) 0.1004(19) Uani 1 1 d . . . . .
F2 F 0.7647(8) 0.7157(6) 0.03375(12) 0.109(2) Uani 1 1 d . . . . .
B1 B 0.7666(9) 0.5944(8) 0.02794(16) 0.0548(17) Uani 1 1 d . . . . .
F3 F 0.8306(12) 0.5840(11) 0.00008(14) 0.175(4) Uani 1 1 d . . . . .
F4 F 0.6271(10) 0.4924(7) 0.0196(2) 0.171(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C4 1.324(6) . ?
N1 C5 1.329(7) . ?
N1 H9 0.8800 . ?
N2 C9 1.315(7) . ?
N2 C10 1.347(7) . ?
N3 C13 1.27(3) . ?
C1 C2 1.539(5) 9 ?
C1 C2 1.539(5) . ?
C1 C7 1.555(5) 9 ?
C1 C7 1.555(5) . ?
C2 C3 1.380(6) . ?
C2 C6 1.413(6) . ?
C3 C4 1.381(6) . ?
C3 H1 0.9500 . ?
C4 H2 0.9500 . ?
C5 C6 1.375(7) . ?
C5 H3 0.9500 . ?
C6 H4 0.9500 . ?
C7 C8 1.388(6) . ?
C7 C11 1.399(6) . ?
C8 C9 1.398(7) . ?
C8 H5 0.9500 . ?
C9 H6 0.9500 . ?
C10 C11 1.369(7) . ?
C10 H7 0.9500 . ?
C11 H8 0.9500 . ?
C12 C13 1.38(3) . ?
C12 H10 0.9806 . ?
C12 H11 0.9806 . ?
C12 H12 0.9806 . ?
C12 H10 0.98(9) 11 ?
C12 H11 0.98(13) 11 ?
C12 H12 1.0(2) 11 ?
F1 B1 1.366(7) . ?
F2 B1 1.317(8) . ?
B1 F3 1.296(9) . ?
B1 F4 1.366(11) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N1 C5 122.4(4) . . ?
C4 N1 H9 118.8 . . ?
C5 N1 H9 118.8 . . ?
C9 N2 C10 117.5(4) . . ?
C2 C1 C2 107.9(5) 9 . ?
C2 C1 C7 109.8(2) 9 9 ?
C2 C1 C7 111.0(2) . 9 ?
C2 C1 C7 111.0(2) 9 . ?
C2 C1 C7 109.8(2) . . ?
C7 C1 C7 107.4(5) 9 . ?
C3 C2 C6 117.4(4) . . ?
C3 C2 C1 123.9(4) . . ?
C6 C2 C1 118.7(3) . . ?
C2 C3 C4 120.3(4) . . ?
C2 C3 H1 119.9 . . ?
C4 C3 H1 119.9 . . ?
N1 C4 C3 120.2(4) . . ?
N1 C4 H2 119.9 . . ?
C3 C4 H2 119.9 . . ?
N1 C5 C6 120.0(4) . . ?
N1 C5 H3 120.0 . . ?
C6 C5 H3 120.0 . . ?
C5 C6 C2 119.8(4) . . ?
C5 C6 H4 120.1 . . ?
C2 C6 H4 120.1 . . ?
C8 C7 C11 117.0(4) . . ?
C8 C7 C1 123.3(4) . . ?
C11 C7 C1 119.7(4) . . ?
C7 C8 C9 118.7(4) . . ?
C7 C8 H5 120.7 . . ?
C9 C8 H5 120.7 . . ?
N2 C9 C8 124.0(5) . . ?
N2 C9 H6 118.0 . . ?
C8 C9 H6 118.0 . . ?
N2 C10 C11 122.7(5) . . ?
N2 C10 H7 118.6 . . ?
C11 C10 H7 118.7 . . ?
C10 C11 C7 120.2(5) . . ?
C10 C11 H8 119.9 . . ?
C7 C11 H8 119.9 . . ?
C13 C12 H10 109.5 . . ?
C13 C12 H11 109.5 . . ?
H10 C12 H11 109.4 . . ?
C13 C12 H12 109.5 . . ?
H10 C12 H12 109.4 . . ?
H11 C12 H12 109.4 . . ?
C13 C12 H10 109.5(18) . 11 ?
H10 C12 H10 140.9 . 11 ?
H11 C12 H10 56.2 . 11 ?
H12 C12 H10 56.2 . 11 ?
C13 C12 H11 110(3) . 11 ?
H10 C12 H11 56.2 . 11 ?
H11 C12 H11 140.9 . 11 ?
H12 C12 H11 56.2 . 11 ?
H10 C12 H11 109.4 11 11 ?
C13 C12 H12 110(4) . 11 ?
H10 C12 H12 56.2 . 11 ?
H11 C12 H12 56.2 . 11 ?
H12 C12 H12 140.9 . 11 ?
H10 C12 H12 109.4 11 11 ?
H11 C12 H12 109.4 11 11 ?
N3 C13 C12 180.0 . . ?
F3 B1 F2 119.1(7) . . ?
F3 B1 F1 110.4(6) . . ?
F2 B1 F1 112.9(5) . . ?
F3 B1 F4 98.4(7) . . ?
F2 B1 F4 105.9(7) . . ?
F1 B1 F4 108.5(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 C2 C3 137.3(5) 9 . . . ?
C7 C1 C2 C3 17.0(5) 9 . . . ?
C7 C1 C2 C3 -101.6(4) . . . . ?
C2 C1 C2 C6 -43.0(3) 9 . . . ?
C7 C1 C2 C6 -163.3(4) 9 . . . ?
C7 C1 C2 C6 78.1(5) . . . . ?
C6 C2 C3 C4 0.9(6) . . . . ?
C1 C2 C3 C4 -179.4(4) . . . . ?
C5 N1 C4 C3 -1.2(7) . . . . ?
C2 C3 C4 N1 0.6(6) . . . . ?
C4 N1 C5 C6 0.2(8) . . . . ?
N1 C5 C6 C2 1.4(8) . . . . ?
C3 C2 C6 C5 -1.8(6) . . . . ?
C1 C2 C6 C5 178.4(4) . . . . ?
C2 C1 C7 C8 106.2(4) 9 . . . ?
C2 C1 C7 C8 -13.0(5) . . . . ?
C7 C1 C7 C8 -133.8(5) 9 . . . ?
C2 C1 C7 C11 -75.4(5) 9 . . . ?
C2 C1 C7 C11 165.5(4) . . . . ?
C7 C1 C7 C11 44.7(3) 9 . . . ?
C11 C7 C8 C9 -1.7(6) . . . . ?
C1 C7 C8 C9 176.8(4) . . . . ?
C10 N2 C9 C8 0.2(7) . . . . ?
C7 C8 C9 N2 0.8(7) . . . . ?
C9 N2 C10 C11 -0.1(8) . . . . ?
N2 C10 C11 C7 -0.9(8) . . . . ?
C8 C7 C11 C10 1.8(7) . . . . ?
C1 C7 C11 C10 -176.8(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H9 N2 0.88 1.89 2.767(5) 170.9 11_665

_refine_diff_density_max         0.507
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.078




data_1_DRY-100K
_database_code_depnum_ccdc_archive 'CCDC 1886469'
_audit_update_record             
;
2018-12-20 deposited with the CCDC.
2018-12-21 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_RINTA01_1_DRY-100K        
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE: During the evaplating of the solvated acetonitrile molecules, the quality of the crystal got somewhat worse.
;
_vrf_PLAT601_1_DRY-100K        
;
PROBLEM: Structure Contains Solvent Accessible VOIDS of .        535 Ang**3
RESPONSE: Measurement was carried out after vacuum drying a crystal in a capillary to evaporate the solvated acetonitrile molecules.
;
# Added during the CSD deposition process: Thursday 20 December 2018 06:54 AM
# end Validation Reply Form


_publ_section_title              
;
?
;

_publ_requested_journal          
;
J. Phys. Chem. C
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6


# SUBMISSION DETAILS 
_publ_contact_author_name        'Yasukazu HIRAO'
_publ_contact_author_address     
;
Department of Chemistry, Graduate School of Science, Osaka University, 
Machikaneyama 1-1, Toyonaka, Osaka 560-0043 (Japan)
;
_publ_contact_author_email       y-hirao@chem.sci.osaka-u.ac.jp
_publ_contact_author_fax         +81-6-6850-5387
_publ_contact_author_phone       +81-6-6850-5385

loop_
_publ_author_name
_publ_author_address
'Inokuchi, Daisuke'
;
Department of Chemistry, Graduate School of Science, Osaka University, 
Machikaneyama 1-1, Toyonaka, Osaka, 560-0043, Japan
;
'Hirao, Yasukazu'
;
Department of Chemistry, Graduate School of Science, Osaka University, 
Machikaneyama 1-1, Toyonaka, Osaka, 560-0043, Japan
;
'Takahashi, Kazuyuki'
;
Department of Chemistry, Graduate School of Science, Kobe University, 
Nada, Hyogo, 657-8501, Japan
;
'Matsumoto, Kouzou'
;
Institute of Natural Sciences, Senshu University, 
Kawasaki, Kanagawa, 214-8580, Japan
;
'Kubo, Takashi'
;
Department of Chemistry, Graduate School of Science, Osaka University, 
Machikaneyama 1-1, Toyonaka, Osaka, 560-0043, Japan
;

_chemical_name_systematic        
;
bis(4-Pyridyl)bis(pyridinium-4-yl)methane bis(tetrafluoroborate) 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H18 N4 2+, (B1 F4 1-)2'
_chemical_formula_sum            'C21 H18 B2 F8 N4'
_chemical_formula_weight         500.01

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      hexagonal
_space_group_IT_number           178
_space_group_name_H-M_alt        'P 61 2 2'
_space_group_name_Hall           'P 61 2 (0 0 -1)'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'x-y, x, z+1/6'
'y, -x+y, z+5/6'
'x-y, -y, -z'
'-x, -x+y, -z+2/3'
'y, x, -z+1/3'
'-y, -x, -z+5/6'
'x, x-y, -z+1/6'
'-x+y, y, -z+1/2'

_cell_length_a                   10.6135(2)
_cell_length_b                   10.6135(2)
_cell_length_c                   38.198(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3726.4(3)
_cell_formula_units_Z            6
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    13976
_cell_measurement_theta_min      3.47
_cell_measurement_theta_max      68.20

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_F_000             1524
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    1.072
_shelx_estimated_absorpt_T_min   0.616
_shelx_estimated_absorpt_T_max   0.739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.0577
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
Empirical Absorption Correction   March 2001 T. Higashi
    Rigaku Corporation, Tokyo, Japan
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus rotating anode'
_diffrn_measurement_device_type  
;
Rigaku VariMax RAPID FR-E
;
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            46326
_diffrn_reflns_av_unetI/netI     0.1247
_diffrn_reflns_av_R_equivalents  0.2658
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_theta_min         4.811
_diffrn_reflns_theta_max         68.240
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2279
_reflns_number_gt                1981
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.567
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    Sir2004
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    
;
Yadokari-XG 2009 (K. Wakita, T. Nemoto, et al., 2009)
;
_computing_publication_material  
;
Yadokari-XG 2009 (K. Wakita, T. Nemoto, et al., 2009)
;
_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)+(0.0073P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 587 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(11)
_chemical_absolute_configuration .
_refine_ls_number_reflns         2279
_refine_ls_number_parameters     196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0559
_refine_ls_wR_factor_ref         0.1145
_refine_ls_wR_factor_gt          0.1101
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4440(3) 0.000000 0.000000 0.0191(9) Uani 1 2 d S T P . .
C2 C 0.5731(3) 0.0848(3) 0.02530(6) 0.0209(6) Uani 1 1 d . . . . .
C3 C 0.5590(3) 0.0847(3) 0.06132(7) 0.0292(7) Uani 1 1 d . . . . .
H3 H 0.465434 0.032496 0.071770 0.035 Uiso 1 1 calc R U . . .
C4 C 0.6816(3) 0.1609(3) 0.08225(8) 0.0374(8) Uani 1 1 d . . . . .
H4 H 0.669148 0.159644 0.106901 0.045 Uiso 1 1 calc R U . . .
N1 N 0.8167(3) 0.2361(3) 0.06915(7) 0.0370(6) Uani 1 1 d . . . . .
C5 C 0.8301(3) 0.2362(3) 0.03435(8) 0.0344(8) Uani 1 1 d . . . . .
H5 H 0.924870 0.289233 0.024562 0.041 Uiso 1 1 calc R U . . .
C6 C 0.7148(3) 0.1640(3) 0.01205(7) 0.0282(7) Uani 1 1 d . . . . .
H6 H 0.730951 0.167599 -0.012487 0.034 Uiso 1 1 calc R U . . .
C7 C 0.3066(3) -0.1029(3) 0.02077(6) 0.0210(6) Uani 1 1 d . . . . .
C8 C 0.2496(3) -0.2521(3) 0.02272(7) 0.0248(7) Uani 1 1 d . . . . .
H8 H 0.297312 -0.296183 0.011290 0.030 Uiso 1 1 calc R U . . .
C9 C 0.1235(3) -0.3361(3) 0.04130(6) 0.0279(7) Uani 1 1 d . . . . .
H9 H 0.084725 -0.438341 0.042638 0.034 Uiso 1 1 calc R U . . .
N2 N 0.0560(2) -0.2766(2) 0.05726(5) 0.0311(6) Uani 1 1 d . . . . .
H2 H -0.024830 -0.332740 0.068811 0.037 Uiso 1 1 calc R U . . .
C10 C 0.1072(3) -0.1331(3) 0.05636(7) 0.0339(7) Uani 1 1 d . . . . .
H10 H 0.056507 -0.093117 0.068224 0.041 Uiso 1 1 calc R U . . .
C11 C 0.2326(3) -0.0433(3) 0.03837(7) 0.0276(7) Uani 1 1 d . . . . .
H11 H 0.269110 0.058705 0.037842 0.033 Uiso 1 1 calc R U . . .
B1 B 0.2812(6) 0.4025(5) 0.02507(11) 0.0486(12) Uani 1 1 d . . . . .
F1 F 0.2755(17) 0.4770(15) 0.0553(3) 0.080(4) Uani 0.438(8) 1 d . . P . .
F2 F 0.3169(14) 0.4764(11) -0.0042(3) 0.098(6) Uani 0.438(8) 1 d . . P . .
F3 F 0.1481(11) 0.2655(13) 0.0164(4) 0.236(8) Uani 0.438(8) 1 d . . P . .
F4 F 0.3557(11) 0.3371(11) 0.03387(18) 0.080(4) Uani 0.438(8) 1 d . . P . .
F5 F 0.2186(12) 0.4478(12) 0.0479(2) 0.089(4) Uani 0.562(8) 1 d . . P . .
F6 F 0.2424(12) 0.4300(11) -0.0042(2) 0.114(4) Uani 0.562(8) 1 d . . P . .
F7 F 0.2465(10) 0.2699(7) 0.03106(17) 0.089(3) Uani 0.562(8) 1 d . . P . .
F8 F 0.4366(5) 0.4825(8) 0.02513(13) 0.095(3) Uani 0.562(8) 1 d . . P . .


_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 C7 1.535(3) . ?
C1 C7 1.535(3) 7 ?
C1 C2 1.545(3) . ?
C1 C2 1.545(3) 7 ?
C2 C3 1.384(3) . ?
C2 C6 1.400(3) . ?
C3 C4 1.391(3) . ?
C3 H3 0.9500 . ?
C4 N1 1.341(3) . ?
C4 H4 0.9500 . ?
N1 C5 1.337(3) . ?
C5 C6 1.368(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.386(3) . ?
C7 C11 1.402(3) . ?
C8 C9 1.377(3) . ?
C8 H8 0.9500 . ?
C9 N2 1.318(3) . ?
C9 H9 0.9500 . ?
N2 C10 1.338(3) . ?
N2 H2 0.8800 . ?
C10 C11 1.373(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
B1 F6 1.274(8) . ?
B1 F7 1.285(6) . ?
B1 F2 1.309(10) . ?
B1 F5 1.324(10) . ?
B1 F4 1.330(7) . ?
B1 F1 1.417(12) . ?
B1 F8 1.428(6) . ?
B1 F3 1.471(11) . ?
F1 F5 0.59(2) . ?
F2 F6 0.691(17) . ?
F2 F8 1.672(12) . ?
F3 F7 1.164(14) . ?
F3 F6 1.710(14) . ?
F4 F7 1.018(8) . ?
F4 F8 1.380(9) . ?

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
C7 C1 C7 107.0(3) . 7 ?
C7 C1 C2 109.98(13) . . ?
C7 C1 C2 111.50(13) 7 . ?
C7 C1 C2 111.50(13) . 7 ?
C7 C1 C2 109.98(13) 7 7 ?
C2 C1 C2 106.9(3) . 7 ?
C3 C2 C6 116.3(2) . . ?
C3 C2 C1 123.9(2) . . ?
C6 C2 C1 119.8(2) . . ?
C2 C3 C4 120.1(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
N1 C4 C3 122.9(3) . . ?
N1 C4 H4 118.6 . . ?
C3 C4 H4 118.6 . . ?
C5 N1 C4 116.9(3) . . ?
N1 C5 C6 123.6(3) . . ?
N1 C5 H5 118.2 . . ?
C6 C5 H5 118.2 . . ?
C5 C6 C2 120.2(3) . . ?
C5 C6 H6 119.9 . . ?
C2 C6 H6 119.9 . . ?
C8 C7 C11 117.9(2) . . ?
C8 C7 C1 123.9(2) . . ?
C11 C7 C1 118.3(2) . . ?
C9 C8 C7 119.7(2) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
N2 C9 C8 120.9(3) . . ?
N2 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 N2 C10 121.7(2) . . ?
C9 N2 H2 119.2 . . ?
C10 N2 H2 119.2 . . ?
N2 C10 C11 120.3(3) . . ?
N2 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C7 119.6(3) . . ?
C10 C11 H11 120.2 . . ?
C7 C11 H11 120.2 . . ?
F6 B1 F7 117.3(7) . . ?
F6 B1 F2 31.0(8) . . ?
F7 B1 F2 130.3(6) . . ?
F6 B1 F5 102.5(8) . . ?
F7 B1 F5 111.0(6) . . ?
F2 B1 F5 113.2(7) . . ?
F6 B1 F4 133.3(6) . . ?
F7 B1 F4 45.8(4) . . ?
F2 B1 F4 117.4(7) . . ?
F5 B1 F4 124.0(6) . . ?
F6 B1 F1 118.5(8) . . ?
F7 B1 F1 113.4(7) . . ?
F2 B1 F1 116.2(8) . . ?
F5 B1 F1 24.7(10) . . ?
F4 B1 F1 106.7(7) . . ?
F6 B1 F8 106.0(6) . . ?
F7 B1 F8 105.3(5) . . ?
F2 B1 F8 75.1(6) . . ?
F5 B1 F8 115.0(6) . . ?
F4 B1 F8 59.9(5) . . ?
F1 B1 F8 91.5(7) . . ?
F6 B1 F3 76.7(8) . . ?
F7 B1 F3 49.4(6) . . ?
F2 B1 F3 104.3(8) . . ?
F5 B1 F3 95.6(7) . . ?
F4 B1 F3 93.9(7) . . ?
F1 B1 F3 116.5(8) . . ?
F8 B1 F3 147.2(6) . . ?
F5 F1 B1 68.8(18) . . ?
F6 F2 B1 71.7(12) . . ?
F6 F2 F8 127.0(15) . . ?
B1 F2 F8 55.7(5) . . ?
F7 F3 B1 56.9(5) . . ?
F7 F3 F6 97.2(7) . . ?
B1 F3 F6 46.5(4) . . ?
F7 F4 B1 64.8(5) . . ?
F7 F4 F8 127.7(8) . . ?
B1 F4 F8 63.6(4) . . ?
F1 F5 B1 86(2) . . ?
F2 F6 B1 77.3(13) . . ?
F2 F6 F3 127.2(16) . . ?
B1 F6 F3 56.8(6) . . ?
F4 F7 F3 139.7(11) . . ?
F4 F7 B1 69.4(6) . . ?
F3 F7 B1 73.6(7) . . ?
F4 F8 B1 56.5(4) . . ?
F4 F8 F2 94.8(5) . . ?
B1 F8 F2 49.2(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
C7 C1 C2 C3 -10.1(3) . . . . ?
C7 C1 C2 C3 108.5(2) 7 . . . ?
C2 C1 C2 C3 -131.2(3) 7 . . . ?
C7 C1 C2 C6 167.9(2) . . . . ?
C7 C1 C2 C6 -73.5(3) 7 . . . ?
C2 C1 C2 C6 46.72(18) 7 . . . ?
C6 C2 C3 C4 0.2(4) . . . . ?
C1 C2 C3 C4 178.2(2) . . . . ?
C2 C3 C4 N1 -0.3(4) . . . . ?
C3 C4 N1 C5 0.3(4) . . . . ?
C4 N1 C5 C6 -0.3(4) . . . . ?
N1 C5 C6 C2 0.2(4) . . . . ?
C3 C2 C6 C5 -0.2(4) . . . . ?
C1 C2 C6 C5 -178.3(2) . . . . ?
C7 C1 C7 C8 134.3(3) 7 . . . ?
C2 C1 C7 C8 -104.4(2) . . . . ?
C2 C1 C7 C8 14.0(3) 7 . . . ?
C7 C1 C7 C11 -44.64(18) 7 . . . ?
C2 C1 C7 C11 76.7(3) . . . . ?
C2 C1 C7 C11 -165.0(2) 7 . . . ?
C11 C7 C8 C9 0.6(4) . . . . ?
C1 C7 C8 C9 -178.4(2) . . . . ?
C7 C8 C9 N2 0.1(4) . . . . ?
C8 C9 N2 C10 -0.6(4) . . . . ?
C9 N2 C10 C11 0.4(4) . . . . ?
N2 C10 C11 C7 0.3(4) . . . . ?
C8 C7 C11 C10 -0.8(4) . . . . ?
C1 C7 C11 C10 178.2(2) . . . . ?
F6 B1 F1 F5 54(3) . . . . ?
F7 B1 F1 F5 -90(2) . . . . ?
F2 B1 F1 F5 89(2) . . . . ?
F4 B1 F1 F5 -138(2) . . . . ?
F8 B1 F1 F5 163(2) . . . . ?
F3 B1 F1 F5 -35(3) . . . . ?
F7 B1 F2 F6 75.9(18) . . . . ?
F5 B1 F2 F6 -75.2(18) . . . . ?
F4 B1 F2 F6 129.7(15) . . . . ?
F1 B1 F2 F6 -102.2(17) . . . . ?
F8 B1 F2 F6 173.6(16) . . . . ?
F3 B1 F2 F6 27.5(17) . . . . ?
F6 B1 F2 F8 -173.6(16) . . . . ?
F7 B1 F2 F8 -97.6(9) . . . . ?
F5 B1 F2 F8 111.2(8) . . . . ?
F4 B1 F2 F8 -43.8(6) . . . . ?
F1 B1 F2 F8 84.2(9) . . . . ?
F3 B1 F2 F8 -146.1(6) . . . . ?
F6 B1 F3 F7 145.5(8) . . . . ?
F2 B1 F3 F7 131.3(8) . . . . ?
F5 B1 F3 F7 -113.0(7) . . . . ?
F4 B1 F3 F7 11.8(7) . . . . ?
F1 B1 F3 F7 -99.1(8) . . . . ?
F8 B1 F3 F7 46.6(16) . . . . ?
F7 B1 F3 F6 -145.5(8) . . . . ?
F2 B1 F3 F6 -14.1(9) . . . . ?
F5 B1 F3 F6 101.5(8) . . . . ?
F4 B1 F3 F6 -133.7(7) . . . . ?
F1 B1 F3 F6 115.4(9) . . . . ?
F8 B1 F3 F6 -98.9(14) . . . . ?
F6 B1 F4 F7 -87.8(12) . . . . ?
F2 B1 F4 F7 -120.9(10) . . . . ?
F5 B1 F4 F7 87.0(10) . . . . ?
F1 B1 F4 F7 106.7(9) . . . . ?
F8 B1 F4 F7 -171.5(8) . . . . ?
F3 B1 F4 F7 -12.5(8) . . . . ?
F6 B1 F4 F8 83.7(10) . . . . ?
F7 B1 F4 F8 171.5(8) . . . . ?
F2 B1 F4 F8 50.7(8) . . . . ?
F5 B1 F4 F8 -101.5(9) . . . . ?
F1 B1 F4 F8 -81.8(8) . . . . ?
F3 B1 F4 F8 159.0(7) . . . . ?
F6 B1 F5 F1 -133(2) . . . . ?
F7 B1 F5 F1 101(2) . . . . ?
F2 B1 F5 F1 -103(2) . . . . ?
F4 B1 F5 F1 50(3) . . . . ?
F8 B1 F5 F1 -19(2) . . . . ?
F3 B1 F5 F1 149(2) . . . . ?
F8 F2 F6 B1 6.7(17) . . . . ?
B1 F2 F6 F3 -28.9(16) . . . . ?
F8 F2 F6 F3 -22(3) . . . . ?
F7 B1 F6 F2 -123.6(15) . . . . ?
F5 B1 F6 F2 114.5(16) . . . . ?
F4 B1 F6 F2 -69.9(19) . . . . ?
F1 B1 F6 F2 94.2(18) . . . . ?
F8 B1 F6 F2 -6.5(16) . . . . ?
F3 B1 F6 F2 -152.6(17) . . . . ?
F7 B1 F6 F3 29.0(7) . . . . ?
F2 B1 F6 F3 152.6(17) . . . . ?
F5 B1 F6 F3 -92.9(8) . . . . ?
F4 B1 F6 F3 82.7(10) . . . . ?
F1 B1 F6 F3 -113.1(10) . . . . ?
F8 B1 F6 F3 146.2(6) . . . . ?
F7 F3 F6 F2 6(2) . . . . ?
B1 F3 F6 F2 34(2) . . . . ?
F7 F3 F6 B1 -28.6(7) . . . . ?
B1 F4 F7 F3 24.9(14) . . . . ?
F8 F4 F7 F3 15.3(19) . . . . ?
F8 F4 F7 B1 -9.6(9) . . . . ?
B1 F3 F7 F4 -24.3(13) . . . . ?
F6 F3 F7 F4 0.2(16) . . . . ?
F6 F3 F7 B1 24.5(5) . . . . ?
F6 B1 F7 F4 125.1(9) . . . . ?
F2 B1 F7 F4 90.9(12) . . . . ?
F5 B1 F7 F4 -117.5(9) . . . . ?
F1 B1 F7 F4 -90.9(9) . . . . ?
F8 B1 F7 F4 7.6(7) . . . . ?
F3 B1 F7 F4 163.5(10) . . . . ?
F6 B1 F7 F3 -38.4(9) . . . . ?
F2 B1 F7 F3 -72.6(12) . . . . ?
F5 B1 F7 F3 79.0(10) . . . . ?
F4 B1 F7 F3 -163.5(10) . . . . ?
F1 B1 F7 F3 105.6(10) . . . . ?
F8 B1 F7 F3 -155.9(8) . . . . ?
F7 F4 F8 B1 9.7(9) . . . . ?
F7 F4 F8 F2 -23.0(11) . . . . ?
B1 F4 F8 F2 -32.7(4) . . . . ?
F6 B1 F8 F4 -131.2(7) . . . . ?
F7 B1 F8 F4 -6.3(6) . . . . ?
F2 B1 F8 F4 -134.7(6) . . . . ?
F5 B1 F8 F4 116.3(7) . . . . ?
F1 B1 F8 F4 108.5(7) . . . . ?
F3 B1 F8 F4 -41.2(15) . . . . ?
F6 B1 F8 F2 3.4(9) . . . . ?
F7 B1 F8 F2 128.4(7) . . . . ?
F5 B1 F8 F2 -109.0(8) . . . . ?
F4 B1 F8 F2 134.7(6) . . . . ?
F1 B1 F8 F2 -116.8(8) . . . . ?
F3 B1 F8 F2 93.5(15) . . . . ?
F6 F2 F8 F4 29(2) . . . . ?
B1 F2 F8 F4 36.5(5) . . . . ?
F6 F2 F8 B1 -7.7(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 N1 0.88 1.83 2.695(3) 169.5 11_445

_refine_diff_density_max         0.230
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.061




data_1_DRY-280K
_database_code_depnum_ccdc_archive 'CCDC 1886470'
_audit_update_record             
;
2018-12-20 deposited with the CCDC.
2018-12-21 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_RINTA01_1_DRY-280K        
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE: During the evaplating of the solvated acetonitrile molecules, the quality of the crystal got somewhat worse.
;
_vrf_PLAT601_1_DRY-280K        
;
PROBLEM: Structure Contains Solvent Accessible VOIDS of .        554 Ang**3
RESPONSE: Measurement was carried out after vacuum drying a crystal in a capillary to evaporate the solvated acetonitrile molecules.
;
# Added during the CSD deposition process: Thursday 20 December 2018 06:54 AM
# end Validation Reply Form


_publ_section_title              
;
?
;

_publ_requested_journal          
;
J. Phys. Chem. C
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6


# SUBMISSION DETAILS 
_publ_contact_author_name        'Yasukazu HIRAO'
_publ_contact_author_address     
;
Department of Chemistry, Graduate School of Science, Osaka University, 
Machikaneyama 1-1, Toyonaka, Osaka 560-0043 (Japan)
;
_publ_contact_author_email       y-hirao@chem.sci.osaka-u.ac.jp
_publ_contact_author_fax         +81-6-6850-5387
_publ_contact_author_phone       +81-6-6850-5385

loop_
_publ_author_name
_publ_author_address
'Inokuchi, Daisuke'
;
Department of Chemistry, Graduate School of Science, Osaka University, 
Machikaneyama 1-1, Toyonaka, Osaka, 560-0043, Japan
;
'Hirao, Yasukazu'
;
Department of Chemistry, Graduate School of Science, Osaka University, 
Machikaneyama 1-1, Toyonaka, Osaka, 560-0043, Japan
;
'Takahashi, Kazuyuki'
;
Department of Chemistry, Graduate School of Science, Kobe University, 
Nada, Hyogo, 657-8501, Japan
;
'Matsumoto, Kouzou'
;
Institute of Natural Sciences, Senshu University, 
Kawasaki, Kanagawa, 214-8580, Japan
;
'Kubo, Takashi'
;
Department of Chemistry, Graduate School of Science, Osaka University, 
Machikaneyama 1-1, Toyonaka, Osaka, 560-0043, Japan
;

_chemical_name_systematic        
;
bis(4-Pyridyl)bis(pyridinium-4-yl)methane bis(tetrafluoroborate) 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H18 N4 2+, (B1 F4 1-)2'
_chemical_formula_sum            'C21 H18 B2 F8 N4'
_chemical_formula_weight         500.01

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      hexagonal
_space_group_IT_number           178
_space_group_name_H-M_alt        'P 61 2 2'
_space_group_name_Hall           'P 61 2 (0 0 -1)'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'x-y, x, z+1/6'
'y, -x+y, z+5/6'
'x-y, -y, -z'
'-x, -x+y, -z+2/3'
'y, x, -z+1/3'
'-y, -x, -z+5/6'
'x, x-y, -z+1/6'
'-x+y, y, -z+1/2'

_cell_length_a                   10.6280(2)
_cell_length_b                   10.6280(2)
_cell_length_c                   38.399(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3756.3(3)
_cell_formula_units_Z            6
_cell_measurement_temperature    280(2)
_cell_measurement_reflns_used    12155
_cell_measurement_theta_min      3.46
_cell_measurement_theta_max      68.18

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_F_000             1524
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    1.064
_shelx_estimated_absorpt_T_min   0.676
_shelx_estimated_absorpt_T_max   0.741
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.0564
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
Empirical Absorption Correction   March 2001 T. Higashi
    Rigaku Corporation, Tokyo, Japan
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      280(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus rotating anode'
_diffrn_measurement_device_type  
;
Rigaku VariMax RAPID FR-E
;
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            46681
_diffrn_reflns_av_unetI/netI     0.1266
_diffrn_reflns_av_R_equivalents  0.2537
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_theta_min         4.805
_diffrn_reflns_theta_max         68.226
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2297
_reflns_number_gt                1852
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.567
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    Sir2004
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    
;
Yadokari-XG 2009 (K. Wakita, T. Nemoto, et al., 2009)
;
_computing_publication_material  
;
Yadokari-XG 2009 (K. Wakita, T. Nemoto, et al., 2009)
;
_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)+(0.0235P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 520 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(12)
_chemical_absolute_configuration .
_refine_ls_number_reflns         2297
_refine_ls_number_parameters     196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0550
_refine_ls_wR_factor_ref         0.1132
_refine_ls_wR_factor_gt          0.1075
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_restrained_S_all      0.974
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.7115(14) 0.1962(11) 0.1120(2) 0.112(4) Uani 0.482(11) 1 d . . P . .
F2 F 0.6423(14) -0.0182(8) 0.1328(2) 0.105(5) Uani 0.482(11) 1 d . . P . .
F3 F 0.6809(15) 0.1564(12) 0.1710(3) 0.125(6) Uani 0.482(11) 1 d . . P . .
F4 F 0.8480(12) 0.1131(18) 0.1470(5) 0.276(10) Uani 0.482(11) 1 d . . P . .
F5 F 0.7951(10) 0.2319(9) 0.1216(2) 0.099(3) Uani 0.518(11) 1 d . . P . .
F6 F 0.5691(7) 0.0493(12) 0.1415(2) 0.143(4) Uani 0.518(11) 1 d . . P . .
F7 F 0.7607(18) 0.1814(11) 0.1710(2) 0.156(6) Uani 0.518(11) 1 d . . P . .
F8 F 0.7513(18) 0.0225(12) 0.1352(3) 0.147(6) Uani 0.518(11) 1 d . . P . .
C1 C 0.5545(3) 0.000000 0.000000 0.0280(8) Uani 1 2 d S T P . .
C2 C 0.4253(3) -0.0852(3) 0.02501(6) 0.0301(6) Uani 1 1 d . . . . .
C3 C 0.2838(3) -0.1642(3) 0.01172(7) 0.0411(7) Uani 1 1 d . . . . .
H3 H 0.268414 -0.168181 -0.012191 0.049 Uiso 1 1 calc R U . . .
C4 C 0.1688(3) -0.2352(3) 0.03373(9) 0.0524(9) Uani 1 1 d . . . . .
H4 H 0.076293 -0.286266 0.024082 0.063 Uiso 1 1 calc R U . . .
N1 N 0.1809(3) -0.2357(3) 0.06824(7) 0.0557(7) Uani 1 1 d . . . . .
C5 C 0.3157(3) -0.1618(3) 0.08149(8) 0.0567(9) Uani 1 1 d . . . . .
H5 H 0.327620 -0.161453 0.105492 0.068 Uiso 1 1 calc R U . . .
C6 C 0.4378(3) -0.0859(3) 0.06071(7) 0.0445(7) Uani 1 1 d . . . . .
H6 H 0.529090 -0.034936 0.070990 0.053 Uiso 1 1 calc R U . . .
C7 C 0.6921(3) 0.1021(3) 0.02093(6) 0.0279(6) Uani 1 1 d . . . . .
C8 C 0.7490(3) 0.2504(3) 0.02328(7) 0.0350(7) Uani 1 1 d . . . . .
H8 H 0.702883 0.294130 0.012189 0.042 Uiso 1 1 calc R U . . .
C9 C 0.8739(3) 0.3333(3) 0.04205(7) 0.0433(7) Uani 1 1 d . . . . .
H9 H 0.911893 0.433193 0.043613 0.052 Uiso 1 1 calc R U . . .
N2 N 0.9405(2) 0.2730(3) 0.05785(5) 0.0443(6) Uani 1 1 d . . . . .
H2 H 1.018849 0.326996 0.069340 0.053 Uiso 1 1 calc R U . . .
C10 C 0.8895(3) 0.1304(3) 0.05648(7) 0.0474(8) Uani 1 1 d . . . . .
H10 H 0.938470 0.090565 0.067961 0.057 Uiso 1 1 calc R U . . .
C11 C 0.7653(3) 0.0420(3) 0.03828(7) 0.0388(7) Uani 1 1 d . . . . .
H11 H 0.729840 -0.057657 0.037443 0.047 Uiso 1 1 calc R U . . .
B1 B 0.7197(7) 0.1203(5) 0.14148(13) 0.0701(14) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 F5 0.857(11) . ?
F1 B1 1.418(9) . ?
F2 F8 1.018(11) . ?
F2 B1 1.321(9) . ?
F2 F6 1.338(10) . ?
F3 F7 0.751(19) . ?
F3 B1 1.327(10) . ?
F3 F6 1.625(12) . ?
F4 F8 1.094(15) . ?
F4 B1 1.419(12) . ?
F4 F7 1.706(17) . ?
F5 B1 1.295(8) . ?
F6 B1 1.387(7) . ?
F7 B1 1.270(9) . ?
F8 B1 1.265(9) . ?
C1 C7 1.540(3) 7 ?
C1 C7 1.540(3) . ?
C1 C2 1.544(3) . ?
C1 C2 1.544(3) 7 ?
C2 C6 1.378(3) . ?
C2 C3 1.402(3) . ?
C3 C4 1.362(4) . ?
C3 H3 0.9300 . ?
C4 N1 1.332(3) . ?
C4 H4 0.9300 . ?
N1 C5 1.343(4) . ?
C5 C6 1.388(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.380(3) . ?
C7 C11 1.398(3) . ?
C8 C9 1.375(3) . ?
C8 H8 0.9300 . ?
C9 N2 1.317(3) . ?
C9 H9 0.9300 . ?
N2 C10 1.331(3) . ?
N2 H2 0.8600 . ?
C10 C11 1.368(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?

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
F5 F1 B1 63.9(9) . . ?
F8 F2 B1 63.9(7) . . ?
F8 F2 F6 126.3(10) . . ?
B1 F2 F6 62.9(5) . . ?
F7 F3 B1 69.1(11) . . ?
F7 F3 F6 123.2(15) . . ?
B1 F3 F6 54.9(5) . . ?
F8 F4 B1 58.7(7) . . ?
F8 F4 F7 97.2(10) . . ?
B1 F4 F7 46.8(6) . . ?
F1 F5 B1 79.6(10) . . ?
F2 F6 B1 57.9(5) . . ?
F2 F6 F3 97.6(6) . . ?
B1 F6 F3 51.5(4) . . ?
F3 F7 B1 77.4(13) . . ?
F3 F7 F4 127.4(16) . . ?
B1 F7 F4 54.6(6) . . ?
F2 F8 F4 141.3(15) . . ?
F2 F8 B1 69.7(8) . . ?
F4 F8 B1 73.6(9) . . ?
C7 C1 C7 106.7(3) 7 . ?
C7 C1 C2 111.72(12) 7 . ?
C7 C1 C2 109.93(12) . . ?
C7 C1 C2 109.94(12) 7 7 ?
C7 C1 C2 111.72(12) . 7 ?
C2 C1 C2 106.9(3) . 7 ?
C6 C2 C3 115.9(2) . . ?
C6 C2 C1 124.2(2) . . ?
C3 C2 C1 119.9(2) . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
N1 C4 C3 123.9(3) . . ?
N1 C4 H4 118.0 . . ?
C3 C4 H4 118.0 . . ?
C4 N1 C5 116.8(3) . . ?
N1 C5 C6 122.4(3) . . ?
N1 C5 H5 118.8 . . ?
C6 C5 H5 118.8 . . ?
C2 C6 C5 120.7(3) . . ?
C2 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C8 C7 C11 117.7(2) . . ?
C8 C7 C1 123.9(2) . . ?
C11 C7 C1 118.4(2) . . ?
C9 C8 C7 119.8(2) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
N2 C9 C8 120.8(3) . . ?
N2 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 N2 C10 121.6(2) . . ?
C9 N2 H2 119.2 . . ?
C10 N2 H2 119.2 . . ?
N2 C10 C11 120.4(2) . . ?
N2 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C7 119.7(2) . . ?
C10 C11 H11 120.1 . . ?
C7 C11 H11 120.1 . . ?
F8 B1 F7 115.1(10) . . ?
F8 B1 F5 110.1(7) . . ?
F7 B1 F5 99.2(9) . . ?
F8 B1 F2 46.3(6) . . ?
F7 B1 F2 131.2(7) . . ?
F5 B1 F2 128.8(7) . . ?
F8 B1 F3 130.4(7) . . ?
F7 B1 F3 33.5(8) . . ?
F5 B1 F3 112.2(7) . . ?
F2 B1 F3 115.3(7) . . ?
F8 B1 F6 105.1(8) . . ?
F7 B1 F6 106.6(8) . . ?
F5 B1 F6 121.1(7) . . ?
F2 B1 F6 59.2(5) . . ?
F3 B1 F6 73.5(6) . . ?
F8 B1 F1 115.6(7) . . ?
F7 B1 F1 121.7(7) . . ?
F5 B1 F1 36.5(5) . . ?
F2 B1 F1 104.5(7) . . ?
F3 B1 F1 113.8(8) . . ?
F6 B1 F1 85.9(7) . . ?
F8 B1 F4 47.7(8) . . ?
F7 B1 F4 78.5(9) . . ?
F5 B1 F4 88.0(8) . . ?
F2 B1 F4 93.2(8) . . ?
F3 B1 F4 109.5(10) . . ?
F6 B1 F4 148.1(8) . . ?
F1 B1 F4 118.9(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F8 F2 F6 B1 8.7(11) . . . . ?
F8 F2 F6 F3 -25.9(14) . . . . ?
B1 F2 F6 F3 -34.6(5) . . . . ?
F7 F3 F6 F2 27(2) . . . . ?
B1 F3 F6 F2 37.9(5) . . . . ?
F7 F3 F6 B1 -11.0(17) . . . . ?
F6 F3 F7 B1 9.6(15) . . . . ?
B1 F3 F7 F4 -23.3(15) . . . . ?
F6 F3 F7 F4 -14(3) . . . . ?
F8 F4 F7 F3 -5(2) . . . . ?
B1 F4 F7 F3 28.3(19) . . . . ?
F8 F4 F7 B1 -33.3(9) . . . . ?
B1 F2 F8 F4 19.4(19) . . . . ?
F6 F2 F8 F4 11(3) . . . . ?
F6 F2 F8 B1 -8.6(11) . . . . ?
B1 F4 F8 F2 -19.0(19) . . . . ?
F7 F4 F8 F2 9(2) . . . . ?
F7 F4 F8 B1 27.9(6) . . . . ?
C7 C1 C2 C6 108.9(2) 7 . . . ?
C7 C1 C2 C6 -9.4(3) . . . . ?
C2 C1 C2 C6 -130.8(3) 7 . . . ?
C7 C1 C2 C3 -73.5(3) 7 . . . ?
C7 C1 C2 C3 168.2(2) . . . . ?
C2 C1 C2 C3 46.78(18) 7 . . . ?
C6 C2 C3 C4 0.2(4) . . . . ?
C1 C2 C3 C4 -177.5(2) . . . . ?
C2 C3 C4 N1 -0.2(5) . . . . ?
C3 C4 N1 C5 -0.4(5) . . . . ?
C4 N1 C5 C6 1.0(5) . . . . ?
C3 C2 C6 C5 0.3(4) . . . . ?
C1 C2 C6 C5 178.0(3) . . . . ?
N1 C5 C6 C2 -1.0(5) . . . . ?
C7 C1 C7 C8 134.4(2) 7 . . . ?
C2 C1 C7 C8 -104.3(2) . . . . ?
C2 C1 C7 C8 14.2(3) 7 . . . ?
C7 C1 C7 C11 -44.74(18) 7 . . . ?
C2 C1 C7 C11 76.6(3) . . . . ?
C2 C1 C7 C11 -164.9(2) 7 . . . ?
C11 C7 C8 C9 0.4(3) . . . . ?
C1 C7 C8 C9 -178.8(2) . . . . ?
C7 C8 C9 N2 0.1(4) . . . . ?
C8 C9 N2 C10 -0.4(4) . . . . ?
C9 N2 C10 C11 0.3(4) . . . . ?
N2 C10 C11 C7 0.2(4) . . . . ?
C8 C7 C11 C10 -0.5(4) . . . . ?
C1 C7 C11 C10 178.7(2) . . . . ?
F2 F8 B1 F7 123.9(11) . . . . ?
F4 F8 B1 F7 -43.6(12) . . . . ?
F2 F8 B1 F5 -125.0(10) . . . . ?
F4 F8 B1 F5 67.5(12) . . . . ?
F4 F8 B1 F2 -167.5(13) . . . . ?
F2 F8 B1 F3 88.0(15) . . . . ?
F4 F8 B1 F3 -79.5(15) . . . . ?
F2 F8 B1 F6 6.9(9) . . . . ?
F4 F8 B1 F6 -160.6(10) . . . . ?
F2 F8 B1 F1 -85.8(10) . . . . ?
F4 F8 B1 F1 106.7(12) . . . . ?
F2 F8 B1 F4 167.5(13) . . . . ?
F3 F7 B1 F8 -126.0(15) . . . . ?
F4 F7 B1 F8 31.3(8) . . . . ?
F3 F7 B1 F5 116.6(15) . . . . ?
F4 F7 B1 F5 -86.1(8) . . . . ?
F3 F7 B1 F2 -73.1(18) . . . . ?
F4 F7 B1 F2 84.2(12) . . . . ?
F4 F7 B1 F3 157.3(16) . . . . ?
F3 F7 B1 F6 -9.8(15) . . . . ?
F4 F7 B1 F6 147.5(8) . . . . ?
F3 F7 B1 F1 85.7(17) . . . . ?
F4 F7 B1 F1 -117.0(11) . . . . ?
F3 F7 B1 F4 -157.3(16) . . . . ?
F1 F5 B1 F8 106.3(15) . . . . ?
F1 F5 B1 F7 -132.6(15) . . . . ?
F1 F5 B1 F2 56.8(16) . . . . ?
F1 F5 B1 F3 -100.4(15) . . . . ?
F1 F5 B1 F6 -16.8(16) . . . . ?
F1 F5 B1 F4 149.4(15) . . . . ?
F6 F2 B1 F8 172.2(10) . . . . ?
F8 F2 B1 F7 -86.8(15) . . . . ?
F6 F2 B1 F7 85.4(12) . . . . ?
F8 F2 B1 F5 80.8(12) . . . . ?
F6 F2 B1 F5 -106.9(10) . . . . ?
F8 F2 B1 F3 -122.6(11) . . . . ?
F6 F2 B1 F3 49.6(8) . . . . ?
F8 F2 B1 F6 -172.2(10) . . . . ?
F8 F2 B1 F1 111.7(10) . . . . ?
F6 F2 B1 F1 -76.0(8) . . . . ?
F8 F2 B1 F4 -9.2(10) . . . . ?
F6 F2 B1 F4 163.0(9) . . . . ?
F7 F3 B1 F8 74.1(19) . . . . ?
F6 F3 B1 F8 -96.1(12) . . . . ?
F6 F3 B1 F7 -170.2(15) . . . . ?
F7 F3 B1 F5 -72.3(17) . . . . ?
F6 F3 B1 F5 117.4(8) . . . . ?
F7 F3 B1 F2 127.2(15) . . . . ?
F6 F3 B1 F2 -43.0(7) . . . . ?
F7 F3 B1 F6 170.2(15) . . . . ?
F7 F3 B1 F1 -112.0(16) . . . . ?
F6 F3 B1 F1 77.8(8) . . . . ?
F7 F3 B1 F4 23.7(16) . . . . ?
F6 F3 B1 F4 -146.5(8) . . . . ?
F2 F6 B1 F8 -5.8(8) . . . . ?
F3 F6 B1 F8 128.3(8) . . . . ?
F2 F6 B1 F7 -128.5(8) . . . . ?
F3 F6 B1 F7 5.6(9) . . . . ?
F2 F6 B1 F5 119.5(9) . . . . ?
F3 F6 B1 F5 -106.4(8) . . . . ?
F3 F6 B1 F2 134.1(7) . . . . ?
F2 F6 B1 F3 -134.1(7) . . . . ?
F2 F6 B1 F1 109.6(6) . . . . ?
F3 F6 B1 F1 -116.3(7) . . . . ?
F2 F6 B1 F4 -33.5(18) . . . . ?
F3 F6 B1 F4 100.6(17) . . . . ?
F5 F1 B1 F8 -89.5(15) . . . . ?
F5 F1 B1 F7 58.7(18) . . . . ?
F5 F1 B1 F2 -137.7(13) . . . . ?
F5 F1 B1 F3 95.7(15) . . . . ?
F5 F1 B1 F6 165.6(13) . . . . ?
F5 F1 B1 F4 -35.6(16) . . . . ?
F7 F4 B1 F8 -140.4(10) . . . . ?
F8 F4 B1 F7 140.4(10) . . . . ?
F8 F4 B1 F5 -119.8(10) . . . . ?
F7 F4 B1 F5 99.8(8) . . . . ?
F8 F4 B1 F2 9.0(9) . . . . ?
F7 F4 B1 F2 -131.4(7) . . . . ?
F8 F4 B1 F3 127.4(10) . . . . ?
F7 F4 B1 F3 -13.1(9) . . . . ?
F8 F4 B1 F6 37(2) . . . . ?
F7 F4 B1 F6 -103.0(17) . . . . ?
F8 F4 B1 F1 -99.5(10) . . . . ?
F7 F4 B1 F1 120.0(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 N1 0.86 1.87 2.717(3) 170.6 11_655

_refine_diff_density_max         0.213
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.057




data_1_Water-100K
_database_code_depnum_ccdc_archive 'CCDC 1886471'
_audit_update_record             
;
2018-12-22 deposited with the CCDC.
2018-12-22 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT430_TPM_H2O-100K        
;
PROBLEM: Short Inter D...A Contact  O5       ..O5       .       1.01 Ang.
RESPONSE: The occupancies of the two oxygen atoms O5 approaching less than the van der Waals radius are 0.5. This is because the solcated water molecules including O5 are statically disordered. O5 occupies one of the two spaces, and never occupies two space at the same time.
;
# Added during the CSD deposition process: Saturday 22 December 2018 07:15 AM
# end Validation Reply Form


_publ_section_title              
;
?
;

_publ_requested_journal          
;
J. Phys. Chem. C
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6


# SUBMISSION DETAILS 
_publ_contact_author_name        'Yasukazu HIRAO'
_publ_contact_author_address     
;
Department of Chemistry, Graduate School of Science, Osaka University, 
Machikaneyama 1-1, Toyonaka, Osaka 560-0043 (Japan)
;
_publ_contact_author_email       y-hirao@chem.sci.osaka-u.ac.jp
_publ_contact_author_fax         +81-6-6850-5387
_publ_contact_author_phone       +81-6-6850-5385

loop_
_publ_author_name
_publ_author_address
'Inokuchi, Daisuke'
;
Department of Chemistry, Graduate School of Science, Osaka University, 
Machikaneyama 1-1, Toyonaka, Osaka, 560-0043, Japan
;
'Hirao, Yasukazu'
;
Department of Chemistry, Graduate School of Science, Osaka University, 
Machikaneyama 1-1, Toyonaka, Osaka, 560-0043, Japan
;
'Takahashi, Kazuyuki'
;
Department of Chemistry, Graduate School of Science, Kobe University, 
Nada, Hyogo, 657-8501, Japan
;
'Matsumoto, Kouzou'
;
Institute of Natural Sciences, Senshu University, 
Kawasaki, Kanagawa, 214-8580, Japan
;
'Kubo, Takashi'
;
Department of Chemistry, Graduate School of Science, Osaka University, 
Machikaneyama 1-1, Toyonaka, Osaka, 560-0043, Japan
;

_chemical_name_systematic        
'bis(4-Pyridyl)bis(pyridinium-4-yl)methane bis(tetrafluoroborate) acetonitrile solvate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H18 N4 2+, (B1 F4 1-)2, 2.5(H2 O1)'
_chemical_formula_sum            'C21 H23 B2 F8 N4 O2.50'
_chemical_formula_weight         545.05

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      hexagonal
_space_group_IT_number           178
_space_group_name_H-M_alt        'P 61 2 2'
_space_group_name_Hall           'P 61 2 (0 0 -1)'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'x-y, x, z+1/6'
'y, -x+y, z+5/6'
'x-y, -y, -z'
'-x, -x+y, -z+2/3'
'y, x, -z+1/3'
'-y, -x, -z+5/6'
'x, x-y, -z+1/6'
'-x+y, y, -z+1/2'

_cell_length_a                   18.3447(3)
_cell_length_b                   18.3447(3)
_cell_length_c                   37.850(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     11031.2(9)
_cell_formula_units_Z            18
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    134010
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      68.26

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_F_000             5022
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    1.211
_shelx_estimated_absorpt_T_min   0.713
_shelx_estimated_absorpt_T_max   0.713
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7751
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
Empirical Absorption Correction   March 2001 T. Higashi
    Rigaku Corporation, Tokyo, Japan
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus rotating anode'
_diffrn_measurement_device_type  
;
Rigaku VariMax RAPID FR-E
;
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            139251
_diffrn_reflns_av_unetI/netI     0.0108
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_theta_min         3.017
_diffrn_reflns_theta_max         68.219
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6748
_reflns_number_gt                6273
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.708
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    Sir2004
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    
;
Yadokari-XG 2009 (K. Wakita, T. Nemoto, et al., 2009)
;
_computing_publication_material  
;
Yadokari-XG 2009 (K. Wakita, T. Nemoto, et al., 2009)
;
_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)+(0.1346P)²+10.1138P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2288 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(14)
_chemical_absolute_configuration .
_refine_ls_number_reflns         6748
_refine_ls_number_parameters     517
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0771
_refine_ls_wR_factor_ref         0.2354
_refine_ls_wR_factor_gt          0.2333
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4055(3) 0.0749(3) 0.16899(9) 0.0518(11) Uani 1 1 d . . . . .
O2 O 0.5523(3) 0.2235(3) 0.15498(17) 0.0872(15) Uani 1 1 d . . . . .
O3 O 0.5934(5) 0.2967(2) 0.083333 0.161(6) Uani 1 2 d S T P . .
O4 O 0.7337(3) 0.7337(3) 0.166667 0.0600(15) Uani 1 2 d S T P . .
O5 O 0.8866(6) 0.8804(5) 0.1797(3) 0.075(3) Uani 0.5 1 d . . P . .
O6 O 0.9214(9) 0.9607(5) 0.083333 0.137(9) Uani 0.5 2 d S T P . .
F1 F 0.0523(3) 0.1623(3) 0.11656(9) 0.0658(11) Uani 1 1 d . . . . .
F2 F -0.0306(2) 0.1945(3) 0.08340(9) 0.0706(12) Uani 1 1 d . . . . .
F3 F -0.0206(2) 0.2181(3) 0.14207(8) 0.0623(11) Uani 1 1 d . . . . .
F4 F 0.0883(3) 0.2955(3) 0.10708(11) 0.0736(12) Uani 1 1 d . . . . .
F5 F 0.3904(2) 0.8378(2) 0.11912(8) 0.0523(9) Uani 1 1 d . . . . .
F6 F 0.3059(2) 0.8662(3) 0.08511(8) 0.0610(10) Uani 1 1 d . . . . .
F7 F 0.3215(2) 0.9003(2) 0.14323(7) 0.0463(8) Uani 1 1 d . . . . .
F8 F 0.4285(2) 0.9716(2) 0.10598(9) 0.0589(9) Uani 1 1 d . . . . .
F9 F 0.6391(3) 0.5300(4) 0.08251(10) 0.0916(16) Uani 1 1 d . . . . .
F10 F 0.7550(3) 0.6265(3) 0.10735(15) 0.1075(18) Uani 1 1 d . . . . .
F11 F 0.6455(3) 0.5515(3) 0.14101(8) 0.0752(13) Uani 1 1 d . . . . .
F12 F 0.7186(3) 0.4956(3) 0.11588(9) 0.0886(16) Uani 1 1 d . . . . .
N1 N 0.0937(2) 0.1956(2) 0.02942(9) 0.0250(7) Uani 1 1 d . . . . .
H25 H 0.059300 0.208635 0.018631 0.030 Uiso 1 1 calc R U . . .
N2 N 0.4289(2) 0.1086(2) 0.00983(10) 0.0298(8) Uani 1 1 d . . . . .
N3 N 0.4256(2) 0.8607(2) 0.02932(8) 0.0250(7) Uani 1 1 d . . . . .
H26 H 0.390994 0.873525 0.018521 0.030 Uiso 1 1 calc R U . . .
N4 N 0.7629(2) 0.7748(2) 0.01035(10) 0.0303(8) Uani 1 1 d . . . . .
N5 N 0.76806(19) 0.5298(2) 0.02896(8) 0.0212(7) Uani 1 1 d . . . . .
H27 H 0.733332 0.542122 0.017922 0.025 Uiso 1 1 calc R U . . .
N6 N 1.1058(2) 0.4448(2) 0.01094(9) 0.0250(7) Uani 1 1 d . . . . .
C1 C 0.2577(3) 0.12884(17) 0.083333 0.0192(11) Uani 1 2 d S T P . .
C2 C 0.2005(2) 0.1551(2) 0.06401(9) 0.0183(8) Uani 1 1 d . . . . .
C3 C 0.1297(3) 0.0939(2) 0.04565(10) 0.0235(8) Uani 1 1 d . . . . .
H1 H 0.118411 0.037419 0.044712 0.028 Uiso 1 1 calc R U . . .
C4 C 0.0769(3) 0.1157(3) 0.02908(11) 0.0269(9) Uani 1 1 d . . . . .
H2 H 0.028057 0.073842 0.017301 0.032 Uiso 1 1 calc R U . . .
C5 C 0.1612(3) 0.2555(2) 0.04568(10) 0.0217(8) Uani 1 1 d . . . . .
H3 H 0.171990 0.311794 0.045067 0.026 Uiso 1 1 calc R U . . .
C6 C 0.2158(2) 0.2376(2) 0.06338(10) 0.0195(8) Uani 1 1 d . . . . .
H4 H 0.263536 0.281126 0.075106 0.023 Uiso 1 1 calc R U . . .
C7 C 0.3156(2) 0.1188(2) 0.05638(9) 0.0192(8) Uani 1 1 d . . . . .
C8 C 0.3843(3) 0.1137(3) 0.06891(11) 0.0243(9) Uani 1 1 d . . . . .
H5 H 0.393839 0.113893 0.093594 0.029 Uiso 1 1 calc R U . . .
C9 C 0.4386(3) 0.1082(2) 0.04499(11) 0.0257(9) Uani 1 1 d . . . . .
H6 H 0.484742 0.103891 0.053869 0.031 Uiso 1 1 calc R U . . .
C10 C 0.3627(3) 0.1126(3) -0.00211(11) 0.0286(9) Uani 1 1 d . . . . .
H7 H 0.354994 0.112476 -0.026933 0.034 Uiso 1 1 calc R U . . .
C11 C 0.3042(3) 0.1171(2) 0.01995(10) 0.0230(8) Uani 1 1 d . . . . .
H8 H 0.257309 0.118880 0.010297 0.028 Uiso 1 1 calc R U . . .
C12 C 0.5906(3) 0.79529(17) 0.083333 0.0181(11) Uani 1 2 d S T P . .
C13 C 0.5333(2) 0.8211(2) 0.06383(9) 0.0195(8) Uani 1 1 d . . . . .
C14 C 0.5483(2) 0.9035(2) 0.06310(9) 0.0186(8) Uani 1 1 d . . . . .
H9 H 0.596106 0.947158 0.074702 0.022 Uiso 1 1 calc R U . . .
C15 C 0.4933(3) 0.9210(2) 0.04549(9) 0.0215(8) Uani 1 1 d . . . . .
H10 H 0.503907 0.977251 0.044855 0.026 Uiso 1 1 calc R U . . .
C16 C 0.4089(3) 0.7803(3) 0.02916(11) 0.0297(9) Uani 1 1 d . . . . .
H11 H 0.360028 0.738145 0.017539 0.036 Uiso 1 1 calc R U . . .
C17 C 0.4620(3) 0.7592(2) 0.04562(10) 0.0241(8) Uani 1 1 d . . . . .
H12 H 0.450913 0.702803 0.044806 0.029 Uiso 1 1 calc R U . . .
C18 C 0.6489(2) 0.7850(2) 0.05664(9) 0.0198(8) Uani 1 1 d . . . . .
C19 C 0.6377(3) 0.7828(2) 0.02013(10) 0.0241(8) Uani 1 1 d . . . . .
H13 H 0.590793 0.784341 0.010370 0.029 Uiso 1 1 calc R U . . .
C20 C 0.6964(3) 0.7784(3) -0.00185(11) 0.0300(10) Uani 1 1 d . . . . .
H14 H 0.688723 0.777957 -0.026688 0.036 Uiso 1 1 calc R U . . .
C21 C 0.7721(3) 0.7745(2) 0.04554(11) 0.0270(9) Uani 1 1 d . . . . .
H15 H 0.818125 0.770282 0.054660 0.032 Uiso 1 1 calc R U . . .
C22 C 0.7172(3) 0.7800(3) 0.06910(11) 0.0252(9) Uani 1 1 d . . . . .
H16 H 0.726469 0.780278 0.093810 0.030 Uiso 1 1 calc R U . . .
C23 C 0.9338(3) 0.46690(14) 0.083333 0.0132(10) Uani 1 2 d S T P . .
C24 C 0.8769(2) 0.4925(2) 0.06370(8) 0.0128(7) Uani 1 1 d . . . . .
C25 C 0.8071(2) 0.4299(2) 0.04498(9) 0.0157(7) Uani 1 1 d . . . . .
H17 H 0.797075 0.373895 0.044161 0.019 Uiso 1 1 calc R U . . .
C26 C 0.7536(2) 0.4506(2) 0.02789(9) 0.0202(8) Uani 1 1 d . . . . .
H18 H 0.706430 0.408688 0.015306 0.024 Uiso 1 1 calc R U . . .
C27 C 0.8335(2) 0.5904(2) 0.04629(9) 0.0190(8) Uani 1 1 d . . . . .
H19 H 0.841957 0.645866 0.046506 0.023 Uiso 1 1 calc R U . . .
C28 C 0.8892(2) 0.5737(2) 0.06387(9) 0.0165(7) Uani 1 1 d . . . . .
H20 H 0.935763 0.617380 0.076086 0.020 Uiso 1 1 calc R U . . .
C29 C 0.9923(2) 0.4562(2) 0.05681(9) 0.0134(7) Uani 1 1 d . . . . .
C30 C 1.0604(2) 0.4505(2) 0.06962(10) 0.0193(8) Uani 1 1 d . . . . .
H21 H 1.069318 0.450414 0.094344 0.023 Uiso 1 1 calc R U . . .
C31 C 1.1150(2) 0.4448(2) 0.04606(10) 0.0208(8) Uani 1 1 d . . . . .
H22 H 1.161064 0.440726 0.055189 0.025 Uiso 1 1 calc R U . . .
C32 C 1.0401(2) 0.4491(3) -0.00145(10) 0.0240(8) Uani 1 1 d . . . . .
H23 H 1.032660 0.448642 -0.026304 0.029 Uiso 1 1 calc R U . . .
C33 C 0.9818(2) 0.4543(2) 0.02036(9) 0.0178(7) Uani 1 1 d . . . . .
H24 H 0.935300 0.456484 0.010466 0.021 Uiso 1 1 calc R U . . .
B1 B 0.0203(3) 0.2144(3) 0.11178(13) 0.0291(11) Uani 1 1 d . . . . .
B2 B 0.3608(3) 0.8922(3) 0.11278(12) 0.0266(10) Uani 1 1 d . . . . .
B3 B 0.6869(3) 0.5471(4) 0.11116(13) 0.0337(12) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O5 O5 1.010(19) 9 ?
F1 B1 1.362(6) . ?
F2 B1 1.349(6) . ?
F3 B1 1.390(5) . ?
F4 B1 1.394(7) . ?
F5 B2 1.375(5) . ?
F6 B2 1.364(6) . ?
F7 B2 1.406(5) . ?
F8 B2 1.386(6) . ?
F9 B3 1.330(6) . ?
F10 B3 1.372(8) . ?
F11 B3 1.386(6) . ?
F12 B3 1.345(6) . ?
N1 C5 1.326(5) . ?
N1 C4 1.338(5) . ?
N1 H25 0.8800 . ?
N2 C10 1.331(6) . ?
N2 C9 1.343(6) . ?
N3 C15 1.329(5) . ?
N3 C16 1.349(5) . ?
N3 H26 0.8800 . ?
N4 C20 1.337(6) . ?
N4 C21 1.343(6) . ?
N5 C27 1.331(5) . ?
N5 C26 1.341(5) . ?
N5 H27 0.8800 . ?
N6 C32 1.333(5) . ?
N6 C31 1.340(5) . ?
C1 C2 1.540(5) 11 ?
C1 C2 1.540(5) . ?
C1 C7 1.550(5) . ?
C1 C7 1.550(5) 11 ?
C2 C6 1.396(5) . ?
C2 C3 1.404(5) . ?
C3 C4 1.371(6) . ?
C3 H1 0.9500 . ?
C4 H2 0.9500 . ?
C5 C6 1.374(5) . ?
C5 H3 0.9500 . ?
C6 H4 0.9500 . ?
C7 C11 1.393(5) . ?
C7 C8 1.393(6) . ?
C8 C9 1.386(6) . ?
C8 H5 0.9500 . ?
C9 H6 0.9500 . ?
C10 C11 1.394(6) . ?
C10 H7 0.9500 . ?
C11 H8 0.9500 . ?
C12 C13 1.539(5) . ?
C12 C13 1.540(5) 11_565 ?
C12 C18 1.550(5) . ?
C12 C18 1.550(5) 11_565 ?
C13 C14 1.395(5) . ?
C13 C17 1.411(5) . ?
C14 C15 1.374(5) . ?
C14 H9 0.9500 . ?
C15 H10 0.9500 . ?
C16 C17 1.365(6) . ?
C16 H11 0.9500 . ?
C17 H12 0.9500 . ?
C18 C22 1.385(6) . ?
C18 C19 1.395(5) . ?
C19 C20 1.394(6) . ?
C19 H13 0.9500 . ?
C20 H14 0.9500 . ?
C21 C22 1.386(6) . ?
C21 H15 0.9500 . ?
C22 H16 0.9500 . ?
C23 C24 1.534(4) . ?
C23 C24 1.534(4) 11 ?
C23 C29 1.551(4) . ?
C23 C29 1.551(4) 11 ?
C24 C28 1.390(5) . ?
C24 C25 1.410(5) . ?
C25 C26 1.378(5) . ?
C25 H17 0.9500 . ?
C26 H18 0.9500 . ?
C27 C28 1.375(5) . ?
C27 H19 0.9500 . ?
C28 H20 0.9500 . ?
C29 C33 1.391(5) . ?
C29 C30 1.394(5) . ?
C30 C31 1.383(5) . ?
C30 H21 0.9500 . ?
C31 H22 0.9500 . ?
C32 C33 1.391(5) . ?
C32 H23 0.9500 . ?
C33 H24 0.9500 . ?

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
C5 N1 C4 121.4(3) . . ?
C5 N1 H25 119.3 . . ?
C4 N1 H25 119.3 . . ?
C10 N2 C9 117.7(4) . . ?
C15 N3 C16 121.2(3) . . ?
C15 N3 H26 119.4 . . ?
C16 N3 H26 119.4 . . ?
C20 N4 C21 117.6(4) . . ?
C27 N5 C26 121.7(3) . . ?
C27 N5 H27 119.1 . . ?
C26 N5 H27 119.1 . . ?
C32 N6 C31 117.8(3) . . ?
C2 C1 C2 107.7(4) 11 . ?
C2 C1 C7 111.21(19) 11 . ?
C2 C1 C7 109.84(18) . . ?
C2 C1 C7 109.84(18) 11 11 ?
C2 C1 C7 111.21(19) . 11 ?
C7 C1 C7 107.1(4) . 11 ?
C6 C2 C3 117.5(3) . . ?
C6 C2 C1 123.3(3) . . ?
C3 C2 C1 119.2(3) . . ?
C4 C3 C2 120.0(4) . . ?
C4 C3 H1 120.0 . . ?
C2 C3 H1 120.0 . . ?
N1 C4 C3 120.3(4) . . ?
N1 C4 H2 119.8 . . ?
C3 C4 H2 119.8 . . ?
N1 C5 C6 121.2(4) . . ?
N1 C5 H3 119.4 . . ?
C6 C5 H3 119.4 . . ?
C5 C6 C2 119.5(4) . . ?
C5 C6 H4 120.2 . . ?
C2 C6 H4 120.2 . . ?
C11 C7 C8 117.8(3) . . ?
C11 C7 C1 123.4(3) . . ?
C8 C7 C1 118.8(3) . . ?
C9 C8 C7 119.3(4) . . ?
C9 C8 H5 120.4 . . ?
C7 C8 H5 120.4 . . ?
N2 C9 C8 123.0(4) . . ?
N2 C9 H6 118.5 . . ?
C8 C9 H6 118.5 . . ?
N2 C10 C11 123.4(4) . . ?
N2 C10 H7 118.3 . . ?
C11 C10 H7 118.3 . . ?
C7 C11 C10 118.8(4) . . ?
C7 C11 H8 120.6 . . ?
C10 C11 H8 120.6 . . ?
C13 C12 C13 107.5(4) . 11_565 ?
C13 C12 C18 110.08(18) . . ?
C13 C12 C18 111.32(19) 11_565 . ?
C13 C12 C18 111.32(19) . 11_565 ?
C13 C12 C18 110.07(18) 11_565 11_565 ?
C18 C12 C18 106.6(4) . 11_565 ?
C14 C13 C17 117.6(3) . . ?
C14 C13 C12 123.2(3) . . ?
C17 C13 C12 119.2(3) . . ?
C15 C14 C13 119.6(4) . . ?
C15 C14 H9 120.2 . . ?
C13 C14 H9 120.2 . . ?
N3 C15 C14 121.2(3) . . ?
N3 C15 H10 119.4 . . ?
C14 C15 H10 119.4 . . ?
N3 C16 C17 120.3(4) . . ?
N3 C16 H11 119.9 . . ?
C17 C16 H11 119.9 . . ?
C16 C17 C13 120.1(4) . . ?
C16 C17 H12 120.0 . . ?
C13 C17 H12 120.0 . . ?
C22 C18 C19 117.4(4) . . ?
C22 C18 C12 119.3(3) . . ?
C19 C18 C12 123.3(3) . . ?
C20 C19 C18 119.1(4) . . ?
C20 C19 H13 120.5 . . ?
C18 C19 H13 120.5 . . ?
N4 C20 C19 123.2(4) . . ?
N4 C20 H14 118.4 . . ?
C19 C20 H14 118.4 . . ?
N4 C21 C22 122.7(4) . . ?
N4 C21 H15 118.6 . . ?
C22 C21 H15 118.6 . . ?
C18 C22 C21 120.0(4) . . ?
C18 C22 H16 120.0 . . ?
C21 C22 H16 120.0 . . ?
C24 C23 C24 107.8(4) . 11 ?
C24 C23 C29 110.15(17) . . ?
C24 C23 C29 111.18(17) 11 . ?
C24 C23 C29 111.17(17) . 11 ?
C24 C23 C29 110.14(17) 11 11 ?
C29 C23 C29 106.5(4) . 11 ?
C28 C24 C25 118.0(3) . . ?
C28 C24 C23 123.7(3) . . ?
C25 C24 C23 118.3(3) . . ?
C26 C25 C24 119.6(3) . . ?
C26 C25 H17 120.2 . . ?
C24 C25 H17 120.2 . . ?
N5 C26 C25 120.2(3) . . ?
N5 C26 H18 119.9 . . ?
C25 C26 H18 119.9 . . ?
N5 C27 C28 120.9(3) . . ?
N5 C27 H19 119.6 . . ?
C28 C27 H19 119.6 . . ?
C27 C28 C24 119.7(3) . . ?
C27 C28 H20 120.1 . . ?
C24 C28 H20 120.1 . . ?
C33 C29 C30 117.5(3) . . ?
C33 C29 C23 123.3(3) . . ?
C30 C29 C23 119.2(3) . . ?
C31 C30 C29 119.5(3) . . ?
C31 C30 H21 120.3 . . ?
C29 C30 H21 120.3 . . ?
N6 C31 C30 123.0(3) . . ?
N6 C31 H22 118.5 . . ?
C30 C31 H22 118.5 . . ?
N6 C32 C33 123.0(4) . . ?
N6 C32 H23 118.5 . . ?
C33 C32 H23 118.5 . . ?
C29 C33 C32 119.3(3) . . ?
C29 C33 H24 120.4 . . ?
C32 C33 H24 120.4 . . ?
F2 B1 F1 113.5(5) . . ?
F2 B1 F3 110.7(4) . . ?
F1 B1 F3 110.9(4) . . ?
F2 B1 F4 108.4(4) . . ?
F1 B1 F4 107.2(4) . . ?
F3 B1 F4 105.7(4) . . ?
F6 B2 F5 111.8(4) . . ?
F6 B2 F8 110.0(4) . . ?
F5 B2 F8 108.9(4) . . ?
F6 B2 F7 109.8(4) . . ?
F5 B2 F7 110.0(3) . . ?
F8 B2 F7 106.2(4) . . ?
F9 B3 F12 114.1(5) . . ?
F9 B3 F10 107.9(5) . . ?
F12 B3 F10 106.0(5) . . ?
F9 B3 F11 111.3(4) . . ?
F12 B3 F11 112.0(4) . . ?
F10 B3 F11 105.0(5) . . ?

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
C2 C1 C2 C6 137.4(4) 11 . . . ?
C7 C1 C2 C6 -101.3(4) . . . . ?
C7 C1 C2 C6 17.1(5) 11 . . . ?
C2 C1 C2 C3 -43.3(3) 11 . . . ?
C7 C1 C2 C3 78.0(4) . . . . ?
C7 C1 C2 C3 -163.6(3) 11 . . . ?
C6 C2 C3 C4 -2.4(6) . . . . ?
C1 C2 C3 C4 178.3(3) . . . . ?
C5 N1 C4 C3 -0.1(6) . . . . ?
C2 C3 C4 N1 2.0(6) . . . . ?
C4 N1 C5 C6 -1.2(6) . . . . ?
N1 C5 C6 C2 0.7(6) . . . . ?
C3 C2 C6 C5 1.1(5) . . . . ?
C1 C2 C6 C5 -179.6(3) . . . . ?
C2 C1 C7 C11 107.1(4) 11 . . . ?
C2 C1 C7 C11 -12.0(5) . . . . ?
C7 C1 C7 C11 -132.9(4) 11 . . . ?
C2 C1 C7 C8 -74.9(4) 11 . . . ?
C2 C1 C7 C8 166.0(3) . . . . ?
C7 C1 C7 C8 45.1(3) 11 . . . ?
C11 C7 C8 C9 0.8(6) . . . . ?
C1 C7 C8 C9 -177.4(3) . . . . ?
C10 N2 C9 C8 -1.6(6) . . . . ?
C7 C8 C9 N2 0.9(6) . . . . ?
C9 N2 C10 C11 0.6(6) . . . . ?
C8 C7 C11 C10 -1.7(6) . . . . ?
C1 C7 C11 C10 176.4(3) . . . . ?
N2 C10 C11 C7 1.1(6) . . . . ?
C13 C12 C13 C14 137.1(4) 11_565 . . . ?
C18 C12 C13 C14 -101.5(4) . . . . ?
C18 C12 C13 C14 16.4(5) 11_565 . . . ?
C13 C12 C13 C17 -43.0(3) 11_565 . . . ?
C18 C12 C13 C17 78.4(4) . . . . ?
C18 C12 C13 C17 -163.7(3) 11_565 . . . ?
C17 C13 C14 C15 1.0(5) . . . . ?
C12 C13 C14 C15 -179.0(3) . . . . ?
C16 N3 C15 C14 -1.0(6) . . . . ?
C13 C14 C15 N3 0.6(5) . . . . ?
C15 N3 C16 C17 -0.3(6) . . . . ?
N3 C16 C17 C13 1.9(6) . . . . ?
C14 C13 C17 C16 -2.3(6) . . . . ?
C12 C13 C17 C16 177.8(4) . . . . ?
C13 C12 C18 C22 166.2(3) . . . . ?
C13 C12 C18 C22 -74.7(5) 11_565 . . . ?
C18 C12 C18 C22 45.4(3) 11_565 . . . ?
C13 C12 C18 C19 -12.0(5) . . . . ?
C13 C12 C18 C19 107.1(4) 11_565 . . . ?
C18 C12 C18 C19 -132.8(4) 11_565 . . . ?
C22 C18 C19 C20 -2.0(6) . . . . ?
C12 C18 C19 C20 176.2(3) . . . . ?
C21 N4 C20 C19 0.8(6) . . . . ?
C18 C19 C20 N4 1.1(6) . . . . ?
C20 N4 C21 C22 -1.8(6) . . . . ?
C19 C18 C22 C21 1.1(6) . . . . ?
C12 C18 C22 C21 -177.2(3) . . . . ?
N4 C21 C22 C18 0.8(6) . . . . ?
C24 C23 C24 C28 134.1(4) 11 . . . ?
C29 C23 C24 C28 -104.5(3) . . . . ?
C29 C23 C24 C28 13.3(4) 11 . . . ?
C24 C23 C24 C25 -44.6(2) 11 . . . ?
C29 C23 C24 C25 76.9(4) . . . . ?
C29 C23 C24 C25 -165.4(3) 11 . . . ?
C28 C24 C25 C26 -0.5(5) . . . . ?
C23 C24 C25 C26 178.3(3) . . . . ?
C27 N5 C26 C25 0.0(5) . . . . ?
C24 C25 C26 N5 0.2(5) . . . . ?
C26 N5 C27 C28 0.0(5) . . . . ?
N5 C27 C28 C24 -0.2(5) . . . . ?
C25 C24 C28 C27 0.5(5) . . . . ?
C23 C24 C28 C27 -178.2(3) . . . . ?
C24 C23 C29 C33 -11.5(4) . . . . ?
C24 C23 C29 C33 107.9(3) 11 . . . ?
C29 C23 C29 C33 -132.1(4) 11 . . . ?
C24 C23 C29 C30 166.7(3) . . . . ?
C24 C23 C29 C30 -73.9(4) 11 . . . ?
C29 C23 C29 C30 46.1(3) 11 . . . ?
C33 C29 C30 C31 1.2(5) . . . . ?
C23 C29 C30 C31 -177.1(3) . . . . ?
C32 N6 C31 C30 -1.1(6) . . . . ?
C29 C30 C31 N6 0.2(6) . . . . ?
C31 N6 C32 C33 0.6(6) . . . . ?
C30 C29 C33 C32 -1.7(5) . . . . ?
C23 C29 C33 C32 176.5(3) . . . . ?
N6 C32 C33 C29 0.9(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H25 N4 0.88 1.84 2.715(5) 170.1 7_565
N5 H27 N6 0.88 1.82 2.696(4) 170.0 7_565

_refine_diff_density_max         1.493
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.100





data_1_Water-296K
_database_code_depnum_ccdc_archive 'CCDC 1886472'
_audit_update_record             
;
2018-12-20 deposited with the CCDC.
2018-12-21 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT260_1_Water-296K        
;
PROBLEM: Large Average Ueq of Residue Including        O2      0.271 Check
RESPONSE: The oxygen atoms O2 of the solvated water molecules are disordered due to the dynamic behavior at the tubular voids of the crystal.
;
# Added during the CSD deposition process: Thursday 20 December 2018 06:54 AM
# end Validation Reply Form


_publ_section_title              
;
?
;

_publ_requested_journal          
;
J. Phys. Chem. C
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6


# SUBMISSION DETAILS 
_publ_contact_author_name        'Yasukazu HIRAO'
_publ_contact_author_address     
;
Department of Chemistry, Graduate School of Science, Osaka University, 
Machikaneyama 1-1, Toyonaka, Osaka 560-0043 (Japan)
;
_publ_contact_author_email       y-hirao@chem.sci.osaka-u.ac.jp
_publ_contact_author_fax         +81-6-6850-5387
_publ_contact_author_phone       +81-6-6850-5385

loop_
_publ_author_name
_publ_author_address
'Inokuchi, Daisuke'
;
Department of Chemistry, Graduate School of Science, Osaka University, 
Machikaneyama 1-1, Toyonaka, Osaka, 560-0043, Japan
;
'Hirao, Yasukazu'
;
Department of Chemistry, Graduate School of Science, Osaka University, 
Machikaneyama 1-1, Toyonaka, Osaka, 560-0043, Japan
;
'Takahashi, Kazuyuki'
;
Department of Chemistry, Graduate School of Science, Kobe University, 
Nada, Hyogo, 657-8501, Japan
;
'Matsumoto, Kouzou'
;
Institute of Natural Sciences, Senshu University, 
Kawasaki, Kanagawa, 214-8580, Japan
;
'Kubo, Takashi'
;
Department of Chemistry, Graduate School of Science, Osaka University, 
Machikaneyama 1-1, Toyonaka, Osaka, 560-0043, Japan
;

_chemical_name_systematic        
'bis(4-Pyridyl)bis(pyridinium-4-yl)methane bis(tetrafluoroborate) acetonitrile solvate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H18 N4 2+, (B1 F4 1-)2, 2.5(H2 O1)'
_chemical_formula_sum            'C21 H23 B2 F8 N4 O2.50'
_chemical_formula_weight         545.05

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      hexagonal
_space_group_IT_number           178
_space_group_name_H-M_alt        'P 61 2 2'
_space_group_name_Hall           'P 61 2 (0 0 -1)'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'x-y, x, z+1/6'
'y, -x+y, z+5/6'
'x-y, -y, -z'
'-x, -x+y, -z+2/3'
'y, x, -z+1/3'
'-y, -x, -z+5/6'
'x, x-y, -z+1/6'
'-x+y, y, -z+1/2'

_cell_length_a                   10.6249(2)
_cell_length_b                   10.6249(2)
_cell_length_c                   38.276(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3742.0(3)
_cell_formula_units_Z            6
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    45964
_cell_measurement_theta_min      3.47
_cell_measurement_theta_max      68.26

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_F_000             1674
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    1.190
_shelx_estimated_absorpt_T_min   0.717
_shelx_estimated_absorpt_T_max   0.717
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7971
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
Empirical Absorption Correction   March 2001 T. Higashi
    Rigaku Corporation, Tokyo, Japan
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus rotating anode'
_diffrn_measurement_device_type  
;
Rigaku VariMax RAPID FR-E
;
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            46762
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_theta_min         4.806
_diffrn_reflns_theta_max         68.253
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2288
_reflns_number_gt                2210
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.567
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    Sir2004
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    
;
Yadokari-XG 2009 (K. Wakita, T. Nemoto, et al., 2009)
;
_computing_publication_material  
;
Yadokari-XG 2009 (K. Wakita, T. Nemoto, et al., 2009)
;
_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)+(0.1624P)²+1.9474P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 792 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(3)
_chemical_absolute_configuration .
_refine_ls_number_reflns         2288
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0781
_refine_ls_wR_factor_ref         0.2271
_refine_ls_wR_factor_gt          0.2258
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.2222(7) 0.4667(6) 0.05578(11) 0.131(2) Uani 1 1 d . . . . .
F2 F 0.2147(11) 0.4393(8) -0.00188(12) 0.183(4) Uani 1 1 d . . . . .
F3 F 0.2401(11) 0.2835(7) 0.03323(14) 0.183(4) Uani 1 1 d . . . . .
F4 F 0.3966(9) 0.4911(13) 0.0236(2) 0.206(4) Uani 1 1 d . . . . .
C1 C 0.4043(5) 0.4043(5) 0.166667 0.0320(10) Uani 1 2 d S T P . .
C2 C 0.2656(4) 0.3707(4) 0.14639(8) 0.0331(8) Uani 1 1 d . . . . .
C3 C 0.2104(4) 0.4646(4) 0.14489(10) 0.0381(8) Uani 1 1 d . . . . .
H3 H 0.258294 0.553816 0.156291 0.046 Uiso 1 1 calc R U . . .
C4 C 0.0851(4) 0.4258(5) 0.12655(11) 0.0446(9) Uani 1 1 d . . . . .
H4 H 0.049086 0.489515 0.125654 0.054 Uiso 1 1 calc R U . . .
C5 C 0.0642(5) 0.2058(5) 0.11080(11) 0.0509(11) Uani 1 1 d . . . . .
H5 H 0.013364 0.117776 0.099031 0.061 Uiso 1 1 calc R U . . .
C6 C 0.1886(4) 0.2383(4) 0.12858(10) 0.0420(9) Uani 1 1 d . . . . .
H6 H 0.222017 0.172385 0.128831 0.050 Uiso 1 1 calc R U . . .
C7 C 0.5328(4) 0.4503(4) 0.14102(9) 0.0352(8) Uani 1 1 d . . . . .
C8 C 0.5164(5) 0.4364(5) 0.10486(10) 0.0450(9) Uani 1 1 d . . . . .
H8 H 0.424465 0.392988 0.094781 0.054 Uiso 1 1 calc R U . . .
C9 C 0.6400(5) 0.4885(6) 0.08414(12) 0.0573(12) Uani 1 1 d . . . . .
H9 H 0.627725 0.478148 0.060045 0.069 Uiso 1 1 calc R U . . .
C10 C 0.7895(5) 0.5624(5) 0.13134(13) 0.0526(11) Uani 1 1 d . . . . .
H10 H 0.882786 0.604811 0.140608 0.063 Uiso 1 1 calc R U . . .
C11 C 0.6738(4) 0.5135(5) 0.15403(11) 0.0445(9) Uani 1 1 d . . . . .
H11 H 0.689836 0.522681 0.178018 0.053 Uiso 1 1 calc R U . . .
N1 N 0.0152(4) 0.3003(4) 0.11024(9) 0.0495(9) Uani 1 1 d . . . . .
H1 H -0.063341 0.278394 0.099031 0.059 Uiso 1 1 calc R U . . .
N2 N 0.7740(4) 0.5519(4) 0.09665(10) 0.0545(10) Uani 1 1 d . . . . .
O1 O 0.4857(10) 0.7429(5) 0.083333 0.115(3) Uani 1 2 d S T P . .
O2 O 0.7920(11) 0.8960(6) 0.083333 0.271(11) Uani 1 2 d S T P . .
O3 O 0.902(2) 1.000000 0.000000 0.169(10) Uani 0.5 2 d S T P . .
B1 B 0.2509(9) 0.4091(7) 0.02734(15) 0.0650(16) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B1 1.356(7) . ?
F2 B1 1.274(8) . ?
F3 B1 1.301(7) . ?
F4 B1 1.352(11) . ?
C1 C2 1.541(4) 9 ?
C1 C2 1.542(4) . ?
C1 C7 1.549(4) . ?
C1 C7 1.549(4) 9 ?
C2 C3 1.389(5) . ?
C2 C6 1.401(5) . ?
C3 C4 1.373(5) . ?
C3 H3 0.9300 . ?
C4 N1 1.315(6) . ?
C4 H4 0.9300 . ?
C5 N1 1.343(6) . ?
C5 C6 1.368(6) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C11 1.392(5) . ?
C7 C8 1.393(5) . ?
C8 C9 1.390(6) . ?
C8 H8 0.9300 . ?
C9 N2 1.323(6) . ?
C9 H9 0.9300 . ?
C10 N2 1.336(6) . ?
C10 C11 1.377(6) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
N1 H1 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C2 107.1(4) 9 . ?
C2 C1 C7 111.53(18) 9 . ?
C2 C1 C7 110.12(18) . . ?
C2 C1 C7 110.12(18) 9 9 ?
C2 C1 C7 111.54(18) . 9 ?
C7 C1 C7 106.5(4) . 9 ?
C3 C2 C6 117.2(3) . . ?
C3 C2 C1 123.5(3) . . ?
C6 C2 C1 119.2(3) . . ?
C4 C3 C2 120.0(4) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
N1 C4 C3 121.3(4) . . ?
N1 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
N1 C5 C6 120.4(4) . . ?
N1 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C2 120.0(4) . . ?
C5 C6 H6 120.0 . . ?
C2 C6 H6 120.0 . . ?
C11 C7 C8 117.0(3) . . ?
C11 C7 C1 119.4(3) . . ?
C8 C7 C1 123.5(3) . . ?
C9 C8 C7 118.8(4) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
N2 C9 C8 123.9(4) . . ?
N2 C9 H9 118.1 . . ?
C8 C9 H9 118.1 . . ?
N2 C10 C11 123.1(4) . . ?
N2 C10 H10 118.5 . . ?
C11 C10 H10 118.5 . . ?
C10 C11 C7 119.9(4) . . ?
C10 C11 H11 120.0 . . ?
C7 C11 H11 120.0 . . ?
C4 N1 C5 121.1(3) . . ?
C4 N1 H1 119.5 . . ?
C5 N1 H1 119.5 . . ?
C9 N2 C10 117.3(4) . . ?
F2 B1 F3 121.8(7) . . ?
F2 B1 F4 97.9(7) . . ?
F3 B1 F4 99.5(8) . . ?
F2 B1 F1 115.3(6) . . ?
F3 B1 F1 113.5(5) . . ?
F4 B1 F1 103.7(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 C2 C3 135.3(4) 9 . . . ?
C7 C1 C2 C3 -103.2(4) . . . . ?
C7 C1 C2 C3 14.8(5) 9 . . . ?
C2 C1 C2 C6 -44.1(3) 9 . . . ?
C7 C1 C2 C6 77.3(4) . . . . ?
C7 C1 C2 C6 -164.7(3) 9 . . . ?
C6 C2 C3 C4 0.2(5) . . . . ?
C1 C2 C3 C4 -179.3(3) . . . . ?
C2 C3 C4 N1 0.1(6) . . . . ?
N1 C5 C6 C2 0.1(7) . . . . ?
C3 C2 C6 C5 -0.3(6) . . . . ?
C1 C2 C6 C5 179.2(4) . . . . ?
C2 C1 C7 C11 -74.2(4) 9 . . . ?
C2 C1 C7 C11 167.0(3) . . . . ?
C7 C1 C7 C11 45.9(3) 9 . . . ?
C2 C1 C7 C8 107.9(4) 9 . . . ?
C2 C1 C7 C8 -10.8(5) . . . . ?
C7 C1 C7 C8 -131.9(4) 9 . . . ?
C11 C7 C8 C9 -1.4(6) . . . . ?
C1 C7 C8 C9 176.5(4) . . . . ?
C7 C8 C9 N2 -0.3(7) . . . . ?
N2 C10 C11 C7 -0.4(7) . . . . ?
C8 C7 C11 C10 1.7(6) . . . . ?
C1 C7 C11 C10 -176.3(4) . . . . ?
C3 C4 N1 C5 -0.3(6) . . . . ?
C6 C5 N1 C4 0.2(7) . . . . ?
C8 C9 N2 C10 1.7(7) . . . . ?
C11 C10 N2 C9 -1.4(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 N2 0.86 1.88 2.738(5) 172.9 11_455

_refine_diff_density_max         0.585
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.078




