#------------------------------------------------------------------------------
#$Date: 2019-11-24 13:40:40 +0200 (Sun, 24 Nov 2019) $
#$Revision: 238036 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/92/4089207.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_4089207
loop_
_publ_author_name
'Grandl, Markus'
'Rudolf, Benjamin'
'Sun, Yu'
'Bechtel, Dominique F.'
'Pierik, Antonio J.'
'Pammer, Frank'
_publ_section_title
;
 Intramolecular N→ B Coordination as a Stabilizing Scaffold for
 π-Conjugated Radical Anions with Tunable Redox Potentials
;
_journal_issue                   14
_journal_name_full               Organometallics
_journal_page_first              2527
_journal_paper_doi               10.1021/acs.organomet.6b00916
_journal_volume                  36
_journal_year                    2017
_chemical_formula_sum            'C27 H20 B F10 N'
_chemical_formula_weight         559.25
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                104.421(5)
_cell_angle_beta                 105.505(5)
_cell_angle_gamma                113.302(6)
_cell_formula_units_Z            2
_cell_length_a                   9.6899(6)
_cell_length_b                   11.8206(7)
_cell_length_c                   12.5661(6)
_cell_measurement_reflns_used    4344
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.8690
_cell_measurement_theta_min      3.3920
_cell_volume                     1166.98(16)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SIR92 (Giacovazzo et al., 1994)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.3385
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.848
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.848
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.848
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.439
_diffrn_reflns_theta_min         2.828
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_description       'transparent prsim'
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.282
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.104
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         5494
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0474
_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)+(0.0346P)²+0.7001P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.1099
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4155
_reflns_number_total             5494
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            om6b00916_si_002.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        1166.97(16)
_cod_database_code               4089207
_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   0.959
_shelx_estimated_absorpt_t_max   0.985
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 1.2150(2) 0.48423(18) 0.79344(16) 0.0187(4) Uani 1 1 d . .
C2 C 1.3450(2) 0.5075(2) 0.75841(17) 0.0238(4) Uani 1 1 d . .
H2 H 1.3218 0.4648 0.6760 0.029 Uiso 1 1 calc R U
C3 C 1.5077(2) 0.5917(2) 0.84128(18) 0.0271(4) Uani 1 1 d . .
H3 H 1.5943 0.6057 0.8153 0.032 Uiso 1 1 calc R U
C4 C 1.5444(2) 0.6557(2) 0.96216(18) 0.0260(4) Uani 1 1 d . .
H4 H 1.6558 0.7146 1.0185 0.031 Uiso 1 1 calc R U
C5 C 1.4185(2) 0.63328(19) 0.99987(17) 0.0221(4) Uani 1 1 d . .
H5 H 1.4431 0.6759 1.0826 0.026 Uiso 1 1 calc R U
C6 C 1.2543(2) 0.54768(19) 0.91638(16) 0.0186(4) Uani 1 1 d . .
C7 C 1.0362(2) 0.39645(18) 0.70506(15) 0.0188(4) Uani 1 1 d . .
H7 H 1.0346 0.4000 0.6261 0.023 Uiso 1 1 calc R U
C8 C 0.9720(2) 0.24542(19) 0.68436(17) 0.0227(4) Uani 1 1 d . .
H8 H 0.8510 0.1951 0.6326 0.027 Uiso 1 1 calc R U
C9 C 0.9961(3) 0.2174(2) 0.79883(18) 0.0263(4) Uani 1 1 d . .
H9A H 0.9571 0.1213 0.7773 0.039 Uiso 1 1 calc R U
H9B H 0.9332 0.2440 0.8389 0.039 Uiso 1 1 calc R U
H9C H 1.1133 0.2691 0.8535 0.039 Uiso 1 1 calc R U
C10 C 1.0531(3) 0.1871(2) 0.61521(19) 0.0313(5) Uani 1 1 d . .
H10A H 0.9981 0.0894 0.5904 0.047 Uiso 1 1 calc R U
H10B H 1.1699 0.2268 0.6673 0.047 Uiso 1 1 calc R U
H10C H 1.0433 0.2079 0.5437 0.047 Uiso 1 1 calc R U
C11 C 1.0163(2) 0.62724(18) 0.75151(15) 0.0179(4) Uani 1 1 d . .
C12 C 1.1039(2) 0.67537(19) 0.68623(15) 0.0199(4) Uani 1 1 d . .
C13 C 1.1589(2) 0.8027(2) 0.68723(16) 0.0225(4) Uani 1 1 d . .
C14 C 1.1305(2) 0.89276(19) 0.75731(17) 0.0250(4) Uani 1 1 d . .
C15 C 1.0453(3) 0.8525(2) 0.82454(17) 0.0253(4) Uani 1 1 d . .
C16 C 0.9903(2) 0.72331(19) 0.81918(16) 0.0212(4) Uani 1 1 d . .
C17 C 0.7368(2) 0.38446(18) 0.65477(15) 0.0165(4) Uani 1 1 d . .
C18 C 0.6237(2) 0.26777(19) 0.65710(16) 0.0200(4) Uani 1 1 d . .
C19 C 0.4588(2) 0.19082(19) 0.57976(17) 0.0232(4) Uani 1 1 d . .
C20 C 0.3963(2) 0.2276(2) 0.49104(16) 0.0227(4) Uani 1 1 d . .
C21 C 0.5016(2) 0.33927(19) 0.48117(15) 0.0187(4) Uani 1 1 d . .
C22 C 0.6657(2) 0.41454(18) 0.56116(15) 0.0169(4) Uani 1 1 d . .
C23 C 1.1221(2) 0.52321(18) 0.95810(15) 0.0174(4) Uani 1 1 d . .
C24 C 0.8520(2) 0.46755(18) 0.92485(15) 0.0181(4) Uani 1 1 d . .
H24 H 0.7457 0.4456 0.8724 0.022 Uiso 1 1 calc R U
N1 N 0.96786(18) 0.48779(15) 0.88225(13) 0.0171(3) Uani 1 1 d . .
F12 F 1.13670(15) 0.59598(11) 0.61131(10) 0.0274(3) Uani 1 1 d . .
F13 F 1.24044(15) 0.83827(12) 0.61914(10) 0.0317(3) Uani 1 1 d . .
F14 F 1.18465(16) 1.01717(12) 0.76058(12) 0.0369(3) Uani 1 1 d . .
F15 F 1.01555(17) 0.93838(13) 0.89406(12) 0.0401(3) Uani 1 1 d . .
F16 F 0.90057(15) 0.69113(12) 0.88454(11) 0.0300(3) Uani 1 1 d . .
F18 F 0.67319(14) 0.22338(11) 0.74144(10) 0.0267(3) Uani 1 1 d . .
F19 F 0.36006(15) 0.08124(12) 0.59064(11) 0.0357(3) Uani 1 1 d . .
F20 F 0.23704(14) 0.15490(12) 0.41452(10) 0.0317(3) Uani 1 1 d . .
F21 F 0.44433(14) 0.37517(11) 0.39313(9) 0.0252(3) Uani 1 1 d . .
F22 F 0.75603(13) 0.52130(11) 0.54175(9) 0.0216(2) Uani 1 1 d . .
B1 B 0.9357(3) 0.4710(2) 0.74190(17) 0.0176(4) Uani 1 1 d . .
C25 C 0.5213(3) 0.9576(2) 0.95863(17) 0.0272(5) Uani 1 1 d . .
H25A H 0.4214 0.8689 0.9069 0.033 Uiso 1 1 calc R U
H25B H 0.6049 0.9423 1.0083 0.033 Uiso 1 1 calc R U
C26 C 0.5872(3) 1.0202(2) 0.87868(19) 0.0333(5) Uani 1 1 d . .
H26A H 0.5057 1.0389 0.8313 0.040 Uiso 1 1 calc R U
H26B H 0.6899 1.1071 0.9302 0.040 Uiso 1 1 calc R U
C27 C 0.6227(3) 0.9316(3) 0.7929(2) 0.0449(6) Uani 1 1 d . .
H27A H 0.7093 0.9181 0.8393 0.067 Uiso 1 1 calc R U
H27B H 0.6595 0.9750 0.7411 0.067 Uiso 1 1 calc R U
H27C H 0.5223 0.8445 0.7429 0.067 Uiso 1 1 calc R U
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_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
C2 C1 C6 117.67(17) . .
C2 C1 C7 122.82(17) . .
C6 C1 C7 119.50(17) . .
C3 C2 C1 121.39(18) . .
C3 C2 H2 119.3 . .
C1 C2 H2 119.3 . .
C2 C3 C4 120.27(19) . .
C2 C3 H3 119.9 . .
C4 C3 H3 119.9 . .
C5 C4 C3 119.69(19) . .
C5 C4 H4 120.2 . .
C3 C4 H4 120.2 . .
C4 C5 C6 120.06(18) . .
C4 C5 H5 120.0 . .
C6 C5 H5 120.0 . .
C5 C6 C1 120.91(18) . .
C5 C6 C23 119.41(16) . .
C1 C6 C23 119.68(16) . .
C1 C7 C8 111.67(15) . .
C1 C7 B1 107.77(14) . .
C8 C7 B1 120.34(16) . .
C1 C7 H7 105.3 . .
C8 C7 H7 105.3 . .
B1 C7 H7 105.3 . .
C10 C8 C9 108.51(16) . .
C10 C8 C7 110.35(17) . .
C9 C8 C7 115.39(15) . .
C10 C8 H8 107.4 . .
C9 C8 H8 107.4 . .
C7 C8 H8 107.4 . .
C8 C9 H9A 109.5 . .
C8 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C8 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C8 C10 H10A 109.5 . .
C8 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C8 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C16 C11 C12 112.02(17) . .
C16 C11 B1 122.66(17) . .
C12 C11 B1 125.08(16) . .
F12 C12 C13 113.99(17) . .
F12 C12 C11 121.28(17) . .
C13 C12 C11 124.68(18) . .
F13 C13 C14 120.09(18) . .
F13 C13 C12 119.82(17) . .
C14 C13 C12 120.09(18) . .
F14 C14 C13 120.94(19) . .
F14 C14 C15 120.58(18) . .
C13 C14 C15 118.47(18) . .
F15 C15 C14 119.87(18) . .
F15 C15 C16 120.75(19) . .
C14 C15 C16 119.38(18) . .
F16 C16 C15 114.88(17) . .
F16 C16 C11 119.75(17) . .
C15 C16 C11 125.34(18) . .
C18 C17 C22 112.22(16) . .
C18 C17 B1 125.13(15) . .
C22 C17 B1 122.39(16) . .
F18 C18 C19 114.93(17) . .
F18 C18 C17 119.79(16) . .
C19 C18 C17 125.27(17) . .
F19 C19 C20 120.01(17) . .
F19 C19 C18 120.56(17) . .
C20 C19 C18 119.43(18) . .
F20 C20 C21 120.67(17) . .
F20 C20 C19 120.83(18) . .
C21 C20 C19 118.48(17) . .
F21 C21 C20 119.58(16) . .
F21 C21 C22 120.07(17) . .
C20 C21 C22 120.35(16) . .
F22 C22 C21 114.59(15) . .
F22 C22 C17 121.21(16) . .
C21 C22 C17 124.20(17) . .
N1 C23 C24 117.81(17) . 2_767
N1 C23 C6 120.77(15) . .
C24 C23 C6 121.41(16) 2_767 .
N1 C24 C23 123.70(16) . 2_767
N1 C24 H24 118.2 . .
C23 C24 H24 118.2 2_767 .
C24 N1 C23 118.47(15) . .
C24 N1 B1 123.87(14) . .
C23 N1 B1 117.66(15) . .
C7 B1 C17 113.19(15) . .
C7 B1 N1 104.29(13) . .
C17 B1 N1 110.52(15) . .
C7 B1 C11 113.10(16) . .
C17 B1 C11 111.08(14) . .
N1 B1 C11 104.04(13) . .
C25 C25 C26 113.8(2) 2_677 .
C25 C25 H25A 108.8 2_677 .
C26 C25 H25A 108.8 . .
C25 C25 H25B 108.8 2_677 .
C26 C25 H25B 108.8 . .
H25A C25 H25B 107.7 . .
C27 C26 C25 113.1(2) . .
C27 C26 H26A 109.0 . .
C25 C26 H26A 109.0 . .
C27 C26 H26B 109.0 . .
C25 C26 H26B 109.0 . .
H26A C26 H26B 107.8 . .
C26 C27 H27A 109.5 . .
C26 C27 H27B 109.5 . .
H27A C27 H27B 109.5 . .
C26 C27 H27C 109.5 . .
H27A C27 H27C 109.5 . .
H27B C27 H27C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.392(3) .
C1 C6 1.406(3) .
C1 C7 1.513(2) .
C2 C3 1.388(3) .
C2 H2 0.9500 .
C3 C4 1.390(3) .
C3 H3 0.9500 .
C4 C5 1.378(3) .
C4 H4 0.9500 .
C5 C6 1.401(3) .
C5 H5 0.9500 .
C6 C23 1.463(3) .
C7 C8 1.564(3) .
C7 B1 1.630(3) .
C7 H7 1.0000 .
C8 C10 1.531(3) .
C8 C9 1.534(3) .
C8 H8 1.0000 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C11 C16 1.391(3) .
C11 C12 1.393(3) .
C11 B1 1.653(3) .
C12 F12 1.351(2) .
C12 C13 1.379(3) .
C13 F13 1.346(2) .
C13 C14 1.371(3) .
C14 F14 1.337(2) .
C14 C15 1.373(3) .
C15 F15 1.342(2) .
C15 C16 1.380(3) .
C16 F16 1.361(2) .
C17 C18 1.395(3) .
C17 C22 1.398(2) .
C17 B1 1.647(3) .
C18 F18 1.354(2) .
C18 C19 1.380(3) .
C19 F19 1.338(2) .
C19 C20 1.374(3) .
C20 F20 1.338(2) .
C20 C21 1.372(3) .
C21 F21 1.343(2) .
C21 C22 1.382(3) .
C22 F22 1.346(2) .
C23 N1 1.364(2) .
C23 C24 1.392(2) 2_767
C24 N1 1.333(2) .
C24 C23 1.392(2) 2_767
C24 H24 0.9500 .
N1 B1 1.652(2) .
C25 C25 1.515(4) 2_677
C25 C26 1.518(3) .
C25 H25A 0.9900 .
C25 H25B 0.9900 .
C26 C27 1.516(3) .
C26 H26A 0.9900 .
C26 H26B 0.9900 .
C27 H27A 0.9800 .
C27 H27B 0.9800 .
C27 H27C 0.9800 .
