#------------------------------------------------------------------------------
#$Date: 2019-11-24 16:48:42 +0200 (Sun, 24 Nov 2019) $
#$Revision: 238643 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/78/7237825.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7237825
loop_
_publ_author_name
'Gao, Ji-Xing'
'Hua, Xiu-Ni'
'Chen, Xiao-Gang'
'Liao, Wei-Qiang'
_publ_section_title
;
 A high temperature optic-electric duple switching organic ionic compound:
 1,4,7-triazoniacyclononane tetrafluoroborate dichloride
;
_journal_issue                   18
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              5348
_journal_paper_doi               10.1039/C9TC01661A
_journal_volume                  7
_journal_year                    2019
_chemical_formula_moiety         'B F4, 3(C2 H6 N), 2(Cl)'
_chemical_formula_sum            'C6 H18 B Cl2 F4 N3'
_chemical_formula_weight         289.94
_space_group_crystal_system      hexagonal
_space_group_IT_number           194
_space_group_name_Hall           '-P 6c 2c'
_space_group_name_H-M_alt        'P 63/m m c'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-03-09 deposited with the CCDC.	2019-04-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            2
_cell_length_a                   8.1276(7)
_cell_length_b                   8.1276(7)
_cell_length_c                   10.5327(13)
_cell_measurement_reflns_used    1742
_cell_measurement_temperature    413(2)
_cell_measurement_theta_max      28.9430
_cell_measurement_theta_min      2.8590
_cell_volume                     602.55(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      413(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'four-circle diffractometer'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2370
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.987
_diffrn_reflns_theta_min         2.894
_diffrn_source                   'Rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    0.567
_exptl_absorpt_correction_T_max  0.863
_exptl_absorpt_correction_T_min  0.858
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_description       Block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.260
_refine_diff_density_max         0.602
_refine_diff_density_min         -0.983
_refine_diff_density_rms         0.146
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.959
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     34
_refine_ls_number_reflns         286
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.938
_refine_ls_R_factor_all          0.1203
_refine_ls_R_factor_gt           0.1161
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3897
_refine_ls_wR_factor_ref         0.3973
_reflns_Friedel_coverage         0.000
_reflns_number_gt                239
_reflns_number_total             286
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9tc01661a2.cif
_cod_data_source_block           P63mmc
_cod_original_cell_volume        602.55(13)
_cod_database_code               7237825
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_min   0.862
_shelx_estimated_absorpt_t_max   0.867
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, z+1/2'
'y, -x+y, z+1/2'
'x-y, x, z+1/2'
'y, x, -z'
'x-y, -y, -z'
'-x, -x+y, -z'
'-y, -x, -z+1/2'
'-x+y, y, -z+1/2'
'x, x-y, -z+1/2'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'x, y, -z-1/2'
'-y, x-y, -z-1/2'
'-x+y, -x, -z-1/2'
'-y, -x, z'
'-x+y, y, z'
'x, x-y, z'
'y, x, z-1/2'
'x-y, -y, z-1/2'
'-x, -x+y, z-1/2'
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
Cl1 Cl 0.6667 0.3333 0.07256(17) 0.0622(16) Uani 1 6 d S T P
B1 B 1.0000 1.0000 0.0000 0.133(8) Uani 1 12 d DS TU P
F1 F 1.0000 1.0000 0.1292(15) 0.171(6) Uani 1 6 d DS TU P
F2 F 0.9026(10) 0.805(2) 0.020(2) 0.143(6) Uani 0.3333 2 d DS TU P
C1 C 0.2931(11) 0.4047(11) 0.260(3) 0.109(7) Uani 0.5 1 d D . P
H1A H 0.3207 0.4521 0.3453 0.3(3) Uiso 0.5 1 d R . P
H1B H 0.2767 0.2792 0.2500 0.072(18) Uiso 1 2 d R . P
N1 N 0.4558(6) 0.5442(6) 0.1820(9) 0.064(3) Uani 0.5 2 d DS T P
H1C H 0.4110 0.5890 0.1210 0.11(6) Uiso 0.5 2 d R . P
H1D H 0.5137 0.4863 0.1457 0.4(6) Uiso 0.5 2 d R . P
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
F1 B1 F1 180.0 . 13_775
F1 B1 F2 98.6(9) . 14_565
F1 B1 F2 81.4(9) 13_775 14_565
F1 B1 F2 81.4(9) . 2_765
F1 B1 F2 98.6(9) 13_775 2_765
F2 B1 F2 180.0(7) 14_565 2_765
F1 B1 F2 98.6(9) . 13_775
F1 B1 F2 81.4(9) 13_775 13_775
F2 B1 F2 117.8(5) 14_565 13_775
F2 B1 F2 62.2(5) 2_765 13_775
F1 B1 F2 81.4(9) . .
F1 B1 F2 98.6(9) 13_775 .
F2 B1 F2 62.2(5) 14_565 .
F2 B1 F2 117.8(5) 2_765 .
F2 B1 F2 180.0 13_775 .
F1 B1 F2 98.6(9) . 15_655
F1 B1 F2 81.4(9) 13_775 15_655
F2 B1 F2 117.8(5) 14_565 15_655
F2 B1 F2 62.2(5) 2_765 15_655
F2 B1 F2 117.8(5) 13_775 15_655
F2 B1 F2 62.2(5) . 15_655
F1 B1 F2 81.4(9) . 3_675
F1 B1 F2 98.6(9) 13_775 3_675
F2 B1 F2 62.2(5) 14_565 3_675
F2 B1 F2 117.8(5) 2_765 3_675
F2 B1 F2 62.2(5) 13_775 3_675
F2 B1 F2 117.8(5) . 3_675
F2 B1 F2 180.0 15_655 3_675
B1 F2 F2 58.9(2) . 14_565
B1 F2 F2 58.9(2) . 15_655
F2 F2 F2 111.9(15) 14_565 15_655
C1 C1 N1 116.3(13) 16_556 16_556
C1 C1 C1 90.007(8) 16_556 20
N1 C1 C1 123.1(7) 16_556 20
C1 C1 N1 56.5(10) 16_556 .
N1 C1 N1 59.8(8) 16_556 .
C1 C1 N1 120.5(5) 20 .
C1 C1 C1 82(2) 16_556 11
N1 C1 C1 127.1(16) 16_556 11
C1 C1 C1 8(2) 20 11
N1 C1 C1 115(2) . 11
C1 N1 C1 125(2) 10_665 16_556
C1 N1 N1 63.7(13) 10_665 16_556
C1 N1 N1 63.7(13) 16_556 16_556
C1 N1 C1 7(2) 10_665 19_665
C1 N1 C1 118.5(7) 16_556 19_665
N1 N1 C1 56.5(10) 16_556 19_665
C1 N1 C1 118.5(7) 10_665 .
C1 N1 C1 7(2) 16_556 .
N1 N1 C1 56.5(10) 16_556 .
C1 N1 C1 111(2) 19_665 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
B1 F1 1.361(16) .
B1 F1 1.361(16) 13_775
B1 F2 1.386(13) 14_565
B1 F2 1.386(13) 2_765
B1 F2 1.386(13) 13_775
B1 F2 1.387(13) .
B1 F2 1.387(13) 15_655
B1 F2 1.387(13) 3_675
F2 F2 1.433(16) 14_565
F2 F2 1.433(16) 15_655
C1 C1 0.21(6) 16_556
C1 N1 1.382(17) 16_556
C1 C1 1.476(17) 20
C1 N1 1.486(18) .
C1 C1 1.491(17) 11
N1 C1 1.382(17) 10_665
N1 C1 1.382(17) 16_556
N1 N1 1.433(19) 16_556
N1 C1 1.486(18) 19_665
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_4
F1 B1 F2 F2 104.6(15) . 14_565
F1 B1 F2 F2 -75.4(15) 13_775 14_565
F2 B1 F2 F2 180.000(0) 2_765 14_565
F2 B1 F2 F2 -151(3) 15_655 14_565
F2 B1 F2 F2 29(3) 3_675 14_565
F1 B1 F2 F2 -104.6(15) . 15_655
F1 B1 F2 F2 75.4(15) 13_775 15_655
F2 B1 F2 F2 151(3) 14_565 15_655
F2 B1 F2 F2 -29(3) 2_765 15_655
F2 B1 F2 F2 180.000(2) 3_675 15_655
C1 C1 N1 C1 164.6(13) 16_556 10_665
N1 C1 N1 C1 -15.4(13) 16_556 10_665
C1 C1 N1 C1 97.6(9) 20 10_665
C1 C1 N1 C1 104(2) 11 10_665
N1 C1 N1 C1 179.993(7) 16_556 16_556
C1 C1 N1 C1 -67.0(8) 20 16_556
C1 C1 N1 C1 -60(3) 11 16_556
C1 C1 N1 N1 -179.993(6) 16_556 16_556
C1 C1 N1 N1 113.0(8) 20 16_556
C1 C1 N1 N1 120(3) 11 16_556
C1 C1 N1 C1 166.5(10) 16_556 19_665
N1 C1 N1 C1 -13.5(10) 16_556 19_665
C1 C1 N1 C1 99.5(10) 20 19_665
C1 C1 N1 C1 106(3) 11 19_665
