#------------------------------------------------------------------------------
#$Date: 2021-04-05 17:22:15 +0300 (Mon, 05 Apr 2021) $
#$Revision: 263694 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/03/1560371.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_1560371
loop_
_publ_author_name
'Stubbe, Jessica'
'Suhr, Simon'
'Beerhues, Julia'
'Nößler, Maite'
'Sarkar, Biprajit'
_publ_section_title
;
 The transformations of a methylene-bridged bis-triazolium salt: a
 mesoionic carbene based metallocage and analogues of TCNE and NacNac
;
_journal_issue                   9
_journal_name_full               'Chemical Science'
_journal_page_first              3170
_journal_page_last               3178
_journal_paper_doi               10.1039/D0SC06957D
_journal_volume                  12
_journal_year                    2021
_chemical_formula_sum            'C9 H15 B F4 N6'
_chemical_formula_weight         294.08
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-I 2y'
_space_group_name_H-M_alt        'I 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2020-08-24 deposited with the CCDC.	2021-02-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.323(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5350(8)
_cell_length_b                   6.4885(5)
_cell_length_c                   18.7172(17)
_cell_measurement_reflns_used    1193
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.366?
_cell_measurement_theta_min      3.323
_cell_volume                     1278.39(18)
_computing_cell_refinement
'APEX3 (Bruker, 2015), CELL_NOW (Sheldrick, 2008)'
_computing_data_collection       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT+ (Bruker, 2009)'
_computing_molecular_graphics    'Diamond 3D, Version 4.0 (Brandenburg, 2014)'
_computing_publication_material  shelxle
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'omega + phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0739
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1452
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.366
_diffrn_reflns_theta_min         3.323
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_T_max  0.745210
_exptl_absorpt_correction_T_min  0.671603
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'twinabs (Sheldrick, 2009)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_description       plate
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.650
_refine_diff_density_min         -0.678
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.574
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1452
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.574
_refine_ls_R_factor_all          0.0844
_refine_ls_R_factor_gt           0.0628
_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)+(0.0529P)²+1.5635P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1506
_refine_ls_wR_factor_ref         0.1569
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1193
_reflns_number_total             1452
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc06957d2.cif
_cod_data_source_block           bip488_twin_I2_m_a
_cod_depositor_comments
'Adding full bibliography for 1560371--1560374.cif.'
_cod_original_sg_symbol_H-M      'I 2/m'
_cod_database_code               1560371
_shelx_shelxl_version_number     2017/1
_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'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, -y+1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
F001 F 0.4178(2) 0.500000 0.69591(12) 0.0239(6) Uani 1 2 d S T P . .
N1 N 0.9911(3) 0.500000 0.69637(17) 0.0140(7) Uani 1 2 d S T P . .
C1 C 0.8123(4) 0.500000 0.5355(2) 0.0193(9) Uani 1 2 d S T P . .
H1A H 0.884829 0.500000 0.504317 0.029 Uiso 1 2 calc . U P . .
H1B H 0.760601 0.623321 0.526012 0.029 Uiso 0.5 1 calc . U P . .
H1C H 0.760601 0.376679 0.526012 0.029 Uiso 0.5 1 calc . U P . .
F002 F 0.33238(18) 0.3253(3) 0.60095(10) 0.0319(6) Uani 1 1 d . . . . .
N2 N 0.9834(3) 0.500000 0.62400(17) 0.0164(8) Uani 1 2 d S T P . .
C2 C 1.1154(4) 0.500000 0.7324(2) 0.0196(9) Uani 1 2 d S T P . .
H2A H 1.181095 0.500000 0.696854 0.029 Uiso 1 2 calc . U P . .
H2B H 1.124547 0.376679 0.762432 0.029 Uiso 0.5 1 calc . U P . .
H2C H 1.124547 0.623321 0.762433 0.029 Uiso 0.5 1 calc . U P . .
N6 N 0.5559(3) 0.500000 0.87381(17) 0.0137(8) Uani 1 2 d S T P . .
F003 F 0.5179(2) 0.500000 0.59080(14) 0.0345(8) Uani 1 2 d S T P . .
N3 N 0.8584(3) 0.500000 0.61045(17) 0.0140(7) Uani 1 2 d S T P . .
C3 C 0.7890(4) 0.500000 0.6691(2) 0.0135(8) Uani 1 2 d S T P . .
H3 H 0.698931 0.500000 0.670530 0.016 Uiso 1 2 calc R U P . .
C4 C 0.8758(4) 0.500000 0.7278(2) 0.0125(8) Uani 1 2 d S T P . .
N4 N 0.7453(3) 0.500000 0.90994(17) 0.0142(7) Uani 1 2 d S T P . .
C5 C 0.8659(4) 0.500000 0.8024(2) 0.0151(9) Uani 1 2 d S T P . .
H5 H 0.942400 0.500000 0.831123 0.018 Uiso 1 2 calc R U P . .
N5 N 0.6262(3) 0.500000 0.93361(17) 0.0150(8) Uani 1 2 d S T P . .
C11 C 0.4166(4) 0.500000 0.8781(2) 0.0178(9) Uani 1 2 d S T P . .
H11A H 0.394102 0.500000 0.928403 0.027 Uiso 1 2 calc . U P . .
H11B H 0.381582 0.376679 0.854407 0.027 Uiso 0.5 1 calc . U P . .
H11C H 0.381582 0.623321 0.854407 0.027 Uiso 0.5 1 calc . U P . .
C12 C 0.8542(4) 0.500000 0.9610(2) 0.0192(9) Uani 1 2 d S T P . .
H12A H 0.823940 0.500000 1.009810 0.029 Uiso 1 2 calc . U P . .
H12B H 0.905761 0.623321 0.953665 0.029 Uiso 0.5 1 calc . U P . .
H12C H 0.905760 0.376679 0.953665 0.029 Uiso 0.5 1 calc . U P . .
C13 C 0.6229(4) 0.500000 0.8141(2) 0.0126(8) Uani 1 2 d S T P . .
H13 H 0.589749 0.500000 0.766116 0.015 Uiso 1 2 calc R U P . .
C14 C 0.7518(4) 0.500000 0.8369(2) 0.0127(8) Uani 1 2 d S T P . .
B00J B 0.4005(4) 0.500000 0.6211(2) 0.0164(10) Uani 1 2 d S T 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'
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
N2 N1 C4 114.3(3) . . ?
N2 N1 C2 118.9(3) . . ?
C4 N1 C2 126.8(3) . . ?
N3 C1 H1A 109.5 . . ?
N3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N3 N2 N1 102.1(3) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N5 N6 C13 114.2(3) . . ?
N5 N6 C11 118.7(3) . . ?
C13 N6 C11 127.1(3) . . ?
N2 N3 C3 114.3(3) . . ?
N2 N3 C1 118.0(3) . . ?
C3 N3 C1 127.7(3) . . ?
N3 C3 C4 106.3(3) . . ?
N3 C3 H3 126.8 . . ?
C4 C3 H3 126.8 . . ?
N1 C4 C3 103.0(3) . . ?
N1 C4 C5 122.0(3) . . ?
C3 C4 C5 135.1(4) . . ?
N5 N4 C14 114.3(3) . . ?
N5 N4 C12 120.1(3) . . ?
C14 N4 C12 125.6(3) . . ?
C14 C5 C4 124.2(4) . . ?
C14 C5 H5 117.9 . . ?
C4 C5 H5 117.9 . . ?
N6 N5 N4 102.7(3) . . ?
N6 C11 H11A 109.5 . . ?
N6 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N6 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N4 C12 H12A 109.5 . . ?
N4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N6 C13 C14 106.3(3) . . ?
N6 C13 H13 126.9 . . ?
C14 C13 H13 126.9 . . ?
N4 C14 C5 122.9(3) . . ?
N4 C14 C13 102.5(3) . . ?
C5 C14 C13 134.6(4) . . ?
F003 B00J F002 110.6(2) . 6_565 ?
F003 B00J F002 110.6(2) . . ?
F002 B00J F002 109.8(3) 6_565 . ?
F003 B00J F001 109.1(3) . . ?
F002 B00J F001 108.4(2) 6_565 . ?
F002 B00J F001 108.4(2) . . ?
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
F001 B00J 1.406(5) . ?
N1 N2 1.354(4) . ?
N1 C4 1.372(5) . ?
N1 C2 1.448(5) . ?
C1 N3 1.466(5) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
F002 B00J 1.386(3) . ?
N2 N3 1.330(5) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
N6 N5 1.317(4) . ?
N6 C13 1.346(5) . ?
N6 C11 1.472(5) . ?
F003 B00J 1.381(5) . ?
N3 C3 1.344(5) . ?
C3 C4 1.401(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.404(5) . ?
N4 N5 1.348(5) . ?
N4 C14 1.372(5) . ?
N4 C12 1.462(5) . ?
C5 C14 1.388(6) . ?
C5 H5 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.407(5) . ?
C13 H13 0.9500 . ?
