#------------------------------------------------------------------------------
#$Date: 2016-11-08 22:12:30 +0200 (Tue, 08 Nov 2016) $
#$Revision: 188258 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/57/7055768.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_7055768
loop_
_publ_author_name
'Jürgens, Eva'
'Buys, Kai N.'
'Schmidt, Anna-Theresa'
'Furfari, Samantha K.'
'Cole, Marcus L.'
'Moser, Michael'
'Rominger, Frank'
'Kunz, Doris'
_publ_section_title
;
 Optimised synthesis of monoanionic bis(NHC)-pincer ligand precursors and
 their Li-complexes
;
_journal_issue                   11
_journal_name_full               'New J. Chem.'
_journal_page_first              9160
_journal_paper_doi               10.1039/C6NJ01941B
_journal_volume                  40
_journal_year                    2016
_chemical_formula_moiety         'C38 H39 N5, 2(B F4)'
_chemical_formula_sum            'C38 H39 B2 F8 N5'
_chemical_formula_weight         739.36
_chemical_name_common            HbimcaPh2HBF4
_chemical_name_systematic
'3,6-Di-tert-butyl-1,8-bis(3-phenylimidazolium)carbazole bis(tetrafluoroborate)'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           57
_space_group_name_Hall           '-P 2c 2b'
_space_group_name_H-M_alt        'P b c m'
_symmetry_space_group_name_Hall  '-P 2c 2b'
_symmetry_space_group_name_H-M   'P b c m'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-04-05 deposited with the CCDC.
2016-09-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.331(2)
_cell_length_b                   10.6223(14)
_cell_length_c                   25.494(3)
_cell_measurement_reflns_used    3797
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.011
_cell_measurement_theta_min      2.078
_cell_volume                     4151.7(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II DUO CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1030
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            89380
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.011
_diffrn_reflns_theta_min         2.078
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.887
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS. Ver. 2014/5. (Krause, L., Herbst-Irmer, R., Sheldrick, G. M. 
& Stalke, D. (2015). J. Appl. Crystallogr. 48.)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_description       plate
_exptl_crystal_F_000             1536
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.025
_exptl_crystal_size_mid          0.015
_exptl_crystal_size_min          0.011
_exptl_transmission_factor_max   1.0000
_exptl_transmission_factor_min   0.8878
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         5633
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.1015
_refine_ls_R_factor_gt           0.0636
_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)+(0.0264P)²+5.3279P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1224
_refine_ls_wR_factor_ref         0.1379
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3797
_reflns_number_total             5633
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6nj01941b2.cif
_cod_data_source_block           phbimca_kwt_sq
_cod_depositor_comments
'Adding full bibliography for 7055764--7055771.cif.'
_cod_database_code               7055768
_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   0.998
_shelx_estimated_absorpt_t_max   0.999
_shelxl_version_number           2013-4
_solvent_exptl_crystal_recrystallization_method Isoproanol
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, z+1/2'
'-x, -y, -z'
'-x, y-1/2, z'
'x, -y-1/2, z-1/2'
'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
F1 F 0.55849(11) 0.27271(13) 0.54317(5) 0.0466(4) Uani 1 1 d . . .
C100 C 0.46955(15) -0.0233(2) 0.40409(8) 0.0270(5) Uani 1 1 d . . .
C311 C 0.9016(3) 0.2412(3) 0.42558(13) 0.0870(14) Uani 1 1 d . . .
H31A H 0.9477 0.2552 0.4515 0.131 Uiso 1 1 calc R U .
H31B H 0.8454 0.2674 0.4403 0.131 Uiso 1 1 calc R U .
H31C H 0.9140 0.2906 0.3940 0.131 Uiso 1 1 calc R U .
F2 F 0.66241(10) 0.35504(14) 0.49009(6) 0.0514(4) Uani 1 1 d . . .
N2 N 0.44698(11) 0.08441(15) 0.37643(6) 0.0223(4) Uani 1 1 d . . .
F3 F 0.38832(9) -0.13662(13) 0.20532(5) 0.0382(3) Uani 1 1 d . . .
N3 N 0.64125(16) 0.0642(2) 0.2500 0.0195(5) Uani 1 2 d S T P
H3N H 0.587(2) 0.053(3) 0.2500 0.023 Uiso 1 2 d S U P
F4 F 0.45731(11) 0.02018(16) 0.2500 0.0274(4) Uani 1 2 d S T P
F5 F 0.51231(13) -0.17924(18) 0.2500 0.0399(5) Uani 1 2 d S T P
N1 N 0.58465(11) 0.05354(15) 0.36398(6) 0.0212(3) Uani 1 1 d . . .
C1 C 0.19731(15) 0.2447(2) 0.37252(11) 0.0410(6) Uani 1 1 d . . .
H1 H 0.1405 0.2804 0.3717 0.049 Uiso 1 1 calc R U .
C2 C 0.25165(15) 0.2562(2) 0.32962(10) 0.0359(5) Uani 1 1 d . . .
H2 H 0.2324 0.3012 0.2996 0.043 Uiso 1 1 calc R U .
C3 C 0.33441(14) 0.2024(2) 0.33016(8) 0.0290(5) Uani 1 1 d . . .
H3 H 0.3717 0.2090 0.3005 0.035 Uiso 1 1 calc R U .
C60 C 0.51805(12) 0.12955(18) 0.35287(7) 0.0206(4) Uani 1 1 d . . .
H60 H 0.5207 0.2032 0.3318 0.025 Uiso 1 1 calc R U .
C7 C 0.67342(13) 0.06939(19) 0.34697(7) 0.0208(4) Uani 1 1 d . . .
C70 C 0.36129(13) 0.13915(19) 0.37470(8) 0.0241(4) Uani 1 1 d . . .
C8 C 0.69408(13) 0.07104(18) 0.29379(7) 0.0204(4) Uani 1 1 d . . .
C9 C 0.30800(16) 0.1281(2) 0.41834(9) 0.0382(6) Uani 1 1 d . . .
H9 H 0.3276 0.0851 0.4488 0.046 Uiso 1 1 calc R U .
C10 C 0.22543(17) 0.1812(3) 0.41661(11) 0.0476(7) Uani 1 1 d . . .
H10 H 0.1878 0.1737 0.4461 0.057 Uiso 1 1 calc R U .
C11 C 0.55480(15) -0.04207(19) 0.39653(7) 0.0259(4) Uani 1 1 d . . .
H11 H 0.5888 -0.1086 0.4108 0.031 Uiso 1 1 calc R U .
C12 C 0.73916(14) 0.07778(19) 0.38393(7) 0.0255(4) Uani 1 1 d . . .
H12 H 0.7243 0.0780 0.4201 0.031 Uiso 1 1 calc R U .
C13 C 0.82746(14) 0.0860(2) 0.36929(8) 0.0259(4) Uani 1 1 d . . .
C14 C 0.84818(13) 0.08693(19) 0.31600(8) 0.0244(4) Uani 1 1 d . . .
H14 H 0.9074 0.0915 0.3053 0.029 Uiso 1 1 calc R U .
C15 C 0.78231(13) 0.08110(19) 0.27850(7) 0.0224(4) Uani 1 1 d . . .
C16 C 0.89789(16) 0.1018(2) 0.41149(8) 0.0362(5) Uani 1 1 d . . .
C17 C 0.98666(17) 0.0576(4) 0.39130(10) 0.0737(12) Uani 1 1 d . . .
H17A H 0.9817 -0.0289 0.3783 0.111 Uiso 1 1 calc R U .
H17B H 1.0293 0.0604 0.4199 0.111 Uiso 1 1 calc R U .
H17C H 1.0059 0.1129 0.3628 0.111 Uiso 1 1 calc R U .
H101 H 0.4263(15) -0.070(2) 0.4240(9) 0.034(6) Uiso 1 1 d . . .
C19 C 0.87649(16) 0.0254(3) 0.46087(9) 0.0421(6) Uani 1 1 d . . .
H19A H 0.8717 -0.0639 0.4517 0.063 Uiso 1 1 calc R U .
H19B H 0.8211 0.0547 0.4756 0.063 Uiso 1 1 calc R U .
H19C H 0.9230 0.0367 0.4868 0.063 Uiso 1 1 calc R U .
B1 B 0.6105(2) 0.2500 0.5000 0.0278(7) Uani 1 2 d S T P
B2 B 0.4352(2) -0.1085(3) 0.2500 0.0211(6) 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_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
C11 C100 N2 107.06(18) . .
C11 C100 H101 132.0(14) . .
N2 C100 H101 120.9(14) . .
C16 C311 H31A 109.5 . .
C16 C311 H31B 109.5 . .
H31A C311 H31B 109.5 . .
C16 C311 H31C 109.5 . .
H31A C311 H31C 109.5 . .
H31B C311 H31C 109.5 . .
C60 N2 C100 108.76(17) . .
C60 N2 C70 125.99(16) . .
C100 N2 C70 125.24(17) . .
C8 N3 C8 107.9(2) . 8_556
C8 N3 H3N 126.00(15) . .
C8 N3 H3N 126.00(15) 8_556 .
C60 N1 C11 108.52(17) . .
C60 N1 C7 126.17(16) . .
C11 N1 C7 125.28(17) . .
C10 C1 C2 120.0(2) . .
C10 C1 H1 120.0 . .
C2 C1 H1 120.0 . .
C1 C2 C3 120.4(2) . .
C1 C2 H2 119.8 . .
C3 C2 H2 119.8 . .
C70 C3 C2 118.7(2) . .
C70 C3 H3 120.7 . .
C2 C3 H3 120.7 . .
N1 C60 N2 108.22(17) . .
N1 C60 H60 125.9 . .
N2 C60 H60 125.9 . .
C12 C7 C8 119.80(18) . .
C12 C7 N1 119.46(17) . .
C8 C7 N1 120.68(17) . .
C3 C70 C9 121.7(2) . .
C3 C70 N2 119.62(18) . .
C9 C70 N2 118.69(19) . .
N3 C8 C7 130.77(19) . .
N3 C8 C15 110.04(17) . .
C7 C8 C15 119.19(17) . .
C10 C9 C70 118.6(2) . .
C10 C9 H9 120.7 . .
C70 C9 H9 120.7 . .
C1 C10 C9 120.7(2) . .
C1 C10 H10 119.7 . .
C9 C10 H10 119.7 . .
C100 C11 N1 107.44(18) . .
C100 C11 H11 126.3 . .
N1 C11 H11 126.3 . .
C7 C12 C13 121.64(18) . .
C7 C12 H12 119.2 . .
C13 C12 H12 119.2 . .
C14 C13 C12 118.54(18) . .
C14 C13 C16 121.47(19) . .
C12 C13 C16 119.88(18) . .
C15 C14 C13 120.22(19) . .
C15 C14 H14 119.9 . .
C13 C14 H14 119.9 . .
C14 C15 C8 120.58(17) . .
C14 C15 C15 133.38(12) . 8_556
C8 C15 C15 106.03(10) . 8_556
C311 C16 C17 110.1(3) . .
C311 C16 C19 109.2(2) . .
C17 C16 C19 107.7(2) . .
C311 C16 C13 107.3(2) . .
C17 C16 C13 110.92(19) . .
C19 C16 C13 111.58(19) . .
C16 C17 H17A 109.5 . .
C16 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C16 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C16 C19 H19A 109.5 . .
C16 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C16 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
F1 B1 F1 109.5(3) 2_556 .
F1 B1 F2 109.54(9) 2_556 2_556
F1 B1 F2 108.98(8) . 2_556
F1 B1 F2 108.98(8) 2_556 .
F1 B1 F2 109.55(9) . .
F2 B1 F2 110.3(3) 2_556 .
F3 B2 F3 111.4(3) . 8_556
F3 B2 F5 108.86(17) . .
F3 B2 F5 108.86(17) 8_556 .
F3 B2 F4 109.61(16) . .
F3 B2 F4 109.61(16) 8_556 .
F5 B2 F4 108.5(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 B1 1.380(2) .
C100 C11 1.336(3) .
C100 N2 1.388(3) .
C100 H101 0.97(2) .
C311 C16 1.525(4) .
C311 H31A 0.9800 .
C311 H31B 0.9800 .
C311 H31C 0.9800 .
F2 B1 1.394(3) .
N2 C60 1.333(2) .
N2 C70 1.437(3) .
F3 B2 1.379(2) .
N3 C8 1.381(2) .
N3 C8 1.381(2) 8_556
N3 H3N 0.85(3) .
F4 B2 1.409(4) .
F5 B2 1.401(4) .
N1 C60 1.332(2) .
N1 C11 1.389(2) .
N1 C7 1.438(3) .
C1 C10 1.380(4) .
C1 C2 1.380(3) .
C1 H1 0.9500 .
C2 C3 1.392(3) .
C2 H2 0.9500 .
C3 C70 1.382(3) .
C3 H3 0.9500 .
C60 H60 0.9500 .
C7 C12 1.382(3) .
C7 C8 1.392(3) .
C70 C9 1.385(3) .
C8 C15 1.412(3) .
C9 C10 1.386(3) .
C9 H9 0.9500 .
C10 H10 0.9500 .
C11 H11 0.9500 .
C12 C13 1.407(3) .
C12 H12 0.9500 .
C13 C14 1.395(3) .
C13 C16 1.533(3) .
C14 C15 1.392(3) .
C14 H14 0.9500 .
C15 C15 1.453(4) 8_556
C16 C17 1.529(4) .
C16 C19 1.533(3) .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
B1 F1 1.380(2) 2_556
B1 F2 1.394(3) 2_556
B2 F3 1.379(2) 8_556
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
C11 C100 N2 C60 -0.3(2) . .
C11 C100 N2 C70 -178.97(18) . .
C10 C1 C2 C3 1.0(4) . .
C1 C2 C3 C70 -1.0(3) . .
C11 N1 C60 N2 -1.0(2) . .
C7 N1 C60 N2 -178.93(17) . .
C100 N2 C60 N1 0.8(2) . .
C70 N2 C60 N1 179.50(17) . .
C60 N1 C7 C12 122.2(2) . .
C11 N1 C7 C12 -55.4(3) . .
C60 N1 C7 C8 -60.5(3) . .
C11 N1 C7 C8 121.9(2) . .
C2 C3 C70 C9 0.1(3) . .
C2 C3 C70 N2 -179.10(19) . .
C60 N2 C70 C3 32.7(3) . .
C100 N2 C70 C3 -148.8(2) . .
C60 N2 C70 C9 -146.5(2) . .
C100 N2 C70 C9 31.9(3) . .
C8 N3 C8 C7 179.41(14) 8_556 .
C8 N3 C8 C15 -0.6(3) 8_556 .
C12 C7 C8 N3 -179.9(2) . .
N1 C7 C8 N3 2.8(3) . .
C12 C7 C8 C15 0.1(3) . .
N1 C7 C8 C15 -177.18(18) . .
C3 C70 C9 C10 0.7(4) . .
N2 C70 C9 C10 179.9(2) . .
C2 C1 C10 C9 -0.2(4) . .
C70 C9 C10 C1 -0.6(4) . .
N2 C100 C11 N1 -0.4(2) . .
C60 N1 C11 C100 0.9(2) . .
C7 N1 C11 C100 178.78(18) . .
C8 C7 C12 C13 -1.0(3) . .
N1 C7 C12 C13 176.27(18) . .
C7 C12 C13 C14 0.7(3) . .
C7 C12 C13 C16 177.0(2) . .
C12 C13 C14 C15 0.6(3) . .
C16 C13 C14 C15 -175.6(2) . .
C13 C14 C15 C8 -1.6(3) . .
C13 C14 C15 C15 179.54(13) . 8_556
N3 C8 C15 C14 -178.8(2) . .
C7 C8 C15 C14 1.2(3) . .
N3 C8 C15 C15 0.37(18) . 8_556
C7 C8 C15 C15 -179.64(15) . 8_556
C14 C13 C16 C311 94.1(3) . .
C12 C13 C16 C311 -82.0(3) . .
C14 C13 C16 C17 -26.2(3) . .
C12 C13 C16 C17 157.6(2) . .
C14 C13 C16 C19 -146.3(2) . .
C12 C13 C16 C19 37.5(3) . .
