#------------------------------------------------------------------------------
#$Date: 2019-11-24 13:40:40 +0200 (Sun, 24 Nov 2019) $
#$Revision: 238036 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/92/4089208.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_4089208
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            'C58 H36 B2 Co F20 N2'
_chemical_formula_weight         1221.44
_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                65.719(14)
_cell_angle_beta                 86.361(11)
_cell_angle_gamma                68.329(14)
_cell_formula_units_Z            1
_cell_length_a                   10.0151(15)
_cell_length_b                   12.0690(18)
_cell_length_c                   12.6447(17)
_cell_measurement_reflns_used    2595
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.8310
_cell_measurement_theta_min      3.2810
_cell_volume                     1287.7(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (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 0.998
_diffrn_measured_fraction_theta_max 0.840
_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  0.0573
_diffrn_reflns_av_unetI/netI     0.1034
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.840
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11620
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.840
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.455
_diffrn_reflns_theta_min         2.969
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.449
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_description       'transparent plate'
_exptl_crystal_F_000             615
_exptl_crystal_size_max          0.308
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.910
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     378
_refine_ls_number_reflns         6004
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1334
_refine_ls_R_factor_gt           0.0751
_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)+(0.0999P)²+0.2589P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1722
_refine_ls_wR_factor_ref         0.2201
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3447
_reflns_number_total             6004
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            om6b00916_si_002.cif
_cod_data_source_block           shelx
_cod_database_code               4089208
_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   0.874
_shelx_estimated_absorpt_t_max   0.961
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
_atom_site_refinement_flags_occupancy
C1 C 0.6477(4) 0.2668(4) -0.0338(3) 0.0209(8) Uani 1 1 d . . .
C2 C 0.5006(4) 0.3427(4) -0.0587(3) 0.0265(9) Uani 1 1 d . . .
H2 H 0.4646 0.4235 -0.0511 0.032 Uiso 1 1 calc R U .
C3 C 0.4058(4) 0.3025(4) -0.0944(3) 0.0314(9) Uani 1 1 d . . .
H3 H 0.3056 0.3557 -0.1108 0.038 Uiso 1 1 calc R U .
C4 C 0.4555(4) 0.1859(4) -0.1065(3) 0.0303(9) Uani 1 1 d . . .
H4 H 0.3898 0.1584 -0.1304 0.036 Uiso 1 1 calc R U .
C5 C 0.6025(4) 0.1087(4) -0.0835(3) 0.0256(8) Uani 1 1 d . . .
H5 H 0.6374 0.0287 -0.0926 0.031 Uiso 1 1 calc R U .
C6 C 0.6995(4) 0.1488(4) -0.0470(3) 0.0218(8) Uani 1 1 d . . .
C7 C 0.7542(4) 0.3012(4) 0.0138(3) 0.0217(8) Uani 1 1 d . . .
H7 H 0.7000 0.3704 0.0417 0.026 Uiso 1 1 calc R U .
C8 C 0.8433(4) 0.3561(4) -0.0869(3) 0.0254(8) Uani 1 1 d . . .
H8 H 0.8627 0.3027 -0.1332 0.030 Uiso 1 1 calc R U .
C9 C 0.9888(4) 0.3502(4) -0.0509(3) 0.0324(10) Uani 1 1 d . . .
H9A H 0.9738 0.4077 -0.0110 0.049 Uiso 1 1 calc R U .
H9B H 1.0383 0.3793 -0.1204 0.049 Uiso 1 1 calc R U .
H9C H 1.0479 0.2598 0.0019 0.049 Uiso 1 1 calc R U .
C10 C 0.7509(5) 0.4970(4) -0.1685(4) 0.0396(11) Uani 1 1 d . . .
H10A H 0.8036 0.5291 -0.2349 0.059 Uiso 1 1 calc R U .
H10B H 0.7293 0.5528 -0.1262 0.059 Uiso 1 1 calc R U .
H10C H 0.6605 0.4997 -0.1968 0.059 Uiso 1 1 calc R U .
C11 C 0.7316(4) 0.1008(4) 0.2079(3) 0.0226(8) Uani 1 1 d . . .
C12 C 0.6218(4) 0.1779(4) 0.2496(3) 0.0257(8) Uani 1 1 d . . .
C13 C 0.5197(4) 0.1364(4) 0.3157(3) 0.0335(10) Uani 1 1 d . . .
C14 C 0.5277(4) 0.0116(4) 0.3459(3) 0.0341(10) Uani 1 1 d . . .
C15 C 0.6365(5) -0.0708(4) 0.3106(3) 0.0314(10) Uani 1 1 d . . .
C16 C 0.7348(4) -0.0252(4) 0.2431(3) 0.0258(8) Uani 1 1 d . . .
C17 C 0.9441(4) 0.1709(4) 0.2216(3) 0.0237(8) Uani 1 1 d . . .
C18 C 1.0309(4) 0.0573(4) 0.3149(3) 0.0261(8) Uani 1 1 d . . .
C19 C 1.1036(4) 0.0566(4) 0.4046(3) 0.0307(10) Uani 1 1 d . . .
C20 C 1.0893(4) 0.1726(5) 0.4064(3) 0.0336(10) Uani 1 1 d . . .
C21 C 1.0008(4) 0.2879(4) 0.3194(3) 0.0298(9) Uani 1 1 d . . .
C22 C 0.9321(4) 0.2846(4) 0.2297(3) 0.0251(8) Uani 1 1 d . . .
C23 C 0.8548(4) 0.0688(3) -0.0217(3) 0.0198(8) Uani 1 1 d . . .
C24 C 1.0762(4) 0.0049(3) 0.0796(3) 0.0208(8) Uani 1 1 d . . .
H24 H 1.1325 0.0086 0.1349 0.025 Uiso 1 1 calc R U .
C25 C 0.3044(6) 0.5191(6) 0.5528(6) 0.0724(18) Uani 1 1 d . . .
H25 H 0.2781 0.4512 0.6090 0.087 Uiso 1 1 calc R U .
C26 C 0.3005(8) 0.5484(15) 0.4404(10) 0.147(5) Uani 1 1 d . . .
H26 H 0.2734 0.5059 0.4016 0.176 Uiso 1 1 calc R U .
C27 C 0.3425(13) 0.6504(13) 0.3917(9) 0.194(9) Uani 1 1 d . . .
H27 H 0.3458 0.6948 0.3103 0.232 Uiso 1 1 calc R U .
C28 C 0.3782(12) 0.6805(9) 0.4707(17) 0.186(8) Uani 1 1 d . . .
H28 H 0.4159 0.7458 0.4591 0.224 Uiso 1 1 calc R U .
C29 C 0.3492(8) 0.5956(8) 0.5767(7) 0.093(2) Uani 1 1 d . . .
H29 H 0.3600 0.5943 0.6513 0.112 Uiso 1 1 calc R U .
N1 N 0.9311(3) 0.0741(3) 0.0640(2) 0.0204(7) Uani 1 1 d . . .
F12 F 0.6096(2) 0.3007(2) 0.22620(18) 0.0354(6) Uani 1 1 d . . .
F13 F 0.4165(3) 0.2160(3) 0.3532(2) 0.0513(8) Uani 1 1 d . . .
F14 F 0.4310(3) -0.0314(3) 0.4114(2) 0.0525(8) Uani 1 1 d . . .
F15 F 0.6492(3) -0.1958(2) 0.3457(2) 0.0429(7) Uani 1 1 d . . .
F16 F 0.8381(3) -0.1135(2) 0.21329(19) 0.0356(6) Uani 1 1 d . . .
F18 F 1.0433(2) -0.0616(2) 0.32346(18) 0.0313(5) Uani 1 1 d . . .
F19 F 1.1843(2) -0.0580(3) 0.49137(18) 0.0406(7) Uani 1 1 d . . .
F20 F 1.1557(3) 0.1759(3) 0.49269(19) 0.0475(7) Uani 1 1 d . . .
F21 F 0.9802(3) 0.4030(3) 0.3227(2) 0.0414(6) Uani 1 1 d . . .
F22 F 0.8444(2) 0.4037(2) 0.15190(19) 0.0347(6) Uani 1 1 d . . .
Co1 Co 0.5000 0.5000 0.5000 0.0384(3) Uani 1 2 d S . P
B1 B 0.8451(4) 0.1644(4) 0.1264(3) 0.0223(9) Uani 1 1 d . . .
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'
Co Co 0.3494 0.9721 '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 118.8(3) . .
C2 C1 C7 123.1(4) . .
C6 C1 C7 117.9(3) . .
C3 C2 C1 121.0(4) . .
C3 C2 H2 119.5 . .
C1 C2 H2 119.5 . .
C4 C3 C2 120.6(4) . .
C4 C3 H3 119.7 . .
C2 C3 H3 119.7 . .
C3 C4 C5 119.6(4) . .
C3 C4 H4 120.2 . .
C5 C4 H4 120.2 . .
C4 C5 C6 120.2(4) . .
C4 C5 H5 119.9 . .
C6 C5 H5 119.9 . .
C1 C6 C5 119.8(3) . .
C1 C6 C23 119.0(3) . .
C5 C6 C23 121.2(3) . .
C1 C7 C8 108.5(3) . .
C1 C7 B1 103.9(3) . .
C8 C7 B1 116.6(3) . .
C1 C7 H7 109.2 . .
C8 C7 H7 109.2 . .
B1 C7 H7 109.2 . .
C9 C8 C10 109.4(3) . .
C9 C8 C7 116.8(3) . .
C10 C8 C7 109.4(3) . .
C9 C8 H8 106.9 . .
C10 C8 H8 106.9 . .
C7 C8 H8 106.9 . .
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 113.8(3) . .
C16 C11 B1 127.4(3) . .
C12 C11 B1 118.8(3) . .
F12 C12 C13 116.1(4) . .
F12 C12 C11 120.1(3) . .
C13 C12 C11 123.8(4) . .
F13 C13 C14 119.8(3) . .
F13 C13 C12 120.7(4) . .
C14 C13 C12 119.4(4) . .
F14 C14 C13 120.4(4) . .
F14 C14 C15 120.0(4) . .
C13 C14 C15 119.6(3) . .
F15 C15 C14 119.6(4) . .
F15 C15 C16 121.0(4) . .
C14 C15 C16 119.4(4) . .
F16 C16 C15 115.0(4) . .
F16 C16 C11 121.0(3) . .
C15 C16 C11 124.0(4) . .
C22 C17 C18 113.2(3) . .
C22 C17 B1 124.5(3) . .
C18 C17 B1 121.4(3) . .
F18 C18 C19 115.9(3) . .
F18 C18 C17 119.8(3) . .
C19 C18 C17 124.3(4) . .
F19 C19 C20 120.3(4) . .
F19 C19 C18 120.1(4) . .
C20 C19 C18 119.6(4) . .
F20 C20 C19 121.4(4) . .
F20 C20 C21 119.6(4) . .
C19 C20 C21 119.0(4) . .
F21 C21 C20 119.8(4) . .
F21 C21 C22 120.5(4) . .
C20 C21 C22 119.7(4) . .
F22 C22 C17 121.6(3) . .
F22 C22 C21 114.1(3) . .
C17 C22 C21 124.2(4) . .
C24 C23 N1 120.5(3) 2_755 .
C24 C23 C6 122.3(3) 2_755 .
N1 C23 C6 117.2(3) . .
C23 C24 N1 124.2(3) 2_755 .
C23 C24 H24 117.9 2_755 .
N1 C24 H24 117.9 . .
C29 C25 C26 111.0(8) . .
C29 C25 Co1 71.4(4) . .
C26 C25 Co1 69.6(4) . .
C29 C25 H25 124.5 . .
C26 C25 H25 124.5 . .
Co1 C25 H25 126.1 . .
C25 C26 C27 106.0(10) . .
C25 C26 Co1 71.6(4) . .
C27 C26 Co1 69.0(6) . .
C25 C26 H26 127.0 . .
C27 C26 H26 127.0 . .
Co1 C26 H26 124.1 . .
C28 C27 C26 111.1(9) . .
C28 C27 Co1 70.7(7) . .
C26 C27 Co1 70.9(5) . .
C28 C27 H27 124.5 . .
C26 C27 H27 124.5 . .
Co1 C27 H27 125.5 . .
C27 C28 C29 105.2(9) . .
C27 C28 Co1 70.1(6) . .
C29 C28 Co1 71.1(5) . .
C27 C28 H28 127.4 . .
C29 C28 H28 127.4 . .
Co1 C28 H28 123.1 . .
C25 C29 C28 106.7(9) . .
C25 C29 Co1 70.5(4) . .
C28 C29 Co1 67.3(5) . .
C25 C29 H29 126.6 . .
C28 C29 H29 126.6 . .
Co1 C29 H29 127.1 . .
C24 N1 C23 115.2(3) . .
C24 N1 B1 126.6(3) . .
C23 N1 B1 118.1(3) . .
C27 Co1 C27 180.0 . 2_666
C27 Co1 C28 140.9(6) . 2_666
C27 Co1 C28 39.1(6) 2_666 2_666
C27 Co1 C28 39.1(6) . .
C27 Co1 C28 140.9(6) 2_666 .
C28 Co1 C28 180.0 2_666 .
C27 Co1 C26 139.9(5) . 2_666
C27 Co1 C26 40.1(5) 2_666 2_666
C28 Co1 C26 67.6(5) 2_666 2_666
C28 Co1 C26 112.4(5) . 2_666
C27 Co1 C26 40.1(5) . .
C27 Co1 C26 139.9(5) 2_666 .
C28 Co1 C26 112.4(5) 2_666 .
C28 Co1 C26 67.6(5) . .
C26 Co1 C26 180.0 2_666 .
C27 Co1 C25 65.2(4) . .
C27 Co1 C25 114.8(4) 2_666 .
C28 Co1 C25 113.1(4) 2_666 .
C28 Co1 C25 66.9(4) . .
C26 Co1 C25 141.2(3) 2_666 .
C26 Co1 C25 38.8(3) . .
C27 Co1 C25 114.8(4) . 2_666
C27 Co1 C25 65.2(4) 2_666 2_666
C28 Co1 C25 66.9(4) 2_666 2_666
C28 Co1 C25 113.1(4) . 2_666
C26 Co1 C25 38.8(3) 2_666 2_666
C26 Co1 C25 141.2(3) . 2_666
C25 Co1 C25 180.0 . 2_666
C27 Co1 C29 66.1(5) . .
C27 Co1 C29 113.9(5) 2_666 .
C28 Co1 C29 138.4(5) 2_666 .
C28 Co1 C29 41.6(5) . .
C26 Co1 C29 114.1(4) 2_666 .
C26 Co1 C29 65.9(4) . .
C25 Co1 C29 38.1(3) . .
C25 Co1 C29 141.9(3) 2_666 .
C27 Co1 C29 113.9(5) . 2_666
C27 Co1 C29 66.1(5) 2_666 2_666
C28 Co1 C29 41.6(5) 2_666 2_666
C28 Co1 C29 138.4(5) . 2_666
C26 Co1 C29 65.9(4) 2_666 2_666
C26 Co1 C29 114.1(4) . 2_666
C25 Co1 C29 141.9(3) . 2_666
C25 Co1 C29 38.1(3) 2_666 2_666
C29 Co1 C29 180.0(5) . 2_666
N1 B1 C7 101.1(3) . .
N1 B1 C17 115.1(3) . .
C7 B1 C17 118.6(3) . .
N1 B1 C11 108.7(3) . .
C7 B1 C11 110.1(3) . .
C17 B1 C11 103.2(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.391(5) .
C1 C6 1.401(5) .
C1 C7 1.513(5) .
C2 C3 1.384(5) .
C2 H2 0.9500 .
C3 C4 1.379(6) .
C3 H3 0.9500 .
C4 C5 1.393(5) .
C4 H4 0.9500 .
C5 C6 1.406(5) .
C5 H5 0.9500 .
C6 C23 1.468(5) .
C7 C8 1.568(5) .
C7 B1 1.643(5) .
C7 H7 1.0000 .
C8 C9 1.522(5) .
C8 C10 1.526(5) .
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 1.386(5) .
C11 C12 1.389(5) .
C11 B1 1.670(5) .
C12 F12 1.345(4) .
C12 C13 1.385(5) .
C13 F13 1.339(5) .
C13 C14 1.366(6) .
C14 F14 1.344(4) .
C14 C15 1.370(6) .
C15 F15 1.344(5) .
C15 C16 1.381(5) .
C16 F16 1.347(4) .
C17 C22 1.379(5) .
C17 C18 1.396(5) .
C17 B1 1.650(6) .
C18 F18 1.352(5) .
C18 C19 1.381(5) .
C19 F19 1.345(5) .
C19 C20 1.364(6) .
C20 F20 1.336(4) .
C20 C21 1.373(6) .
C21 F21 1.345(5) .
C21 C22 1.385(5) .
C22 F22 1.349(4) .
C23 C24 1.349(5) 2_755
C23 N1 1.401(4) .
C24 C23 1.349(5) 2_755
C24 N1 1.361(4) .
C24 H24 0.9500 .
C25 C29 1.303(9) .
C25 C26 1.315(11) .
C25 Co1 1.990(6) .
C25 H25 0.9500 .
C26 C27 1.341(17) .
C26 Co1 1.967(7) .
C26 H26 0.9500 .
C27 C28 1.30(2) .
C27 Co1 1.942(8) .
C27 H27 0.9500 .
C28 C29 1.404(16) .
C28 Co1 1.950(9) .
C28 H28 0.9500 .
C29 Co1 2.000(6) .
C29 H29 0.9500 .
N1 B1 1.575(5) .
Co1 C27 1.942(8) 2_666
Co1 C28 1.950(9) 2_666
Co1 C26 1.967(7) 2_666
Co1 C25 1.990(6) 2_666
Co1 C29 2.000(6) 2_666
