An isolable boron-centered radical anion stabilized by a carbazole moiety.
Yuan, Ningning; Zhu, Tingchun; Ma, Jianping; Xue, Yunsheng; Liu, Yirui; Dalton transactions (Cambridge, England : 2003) 54 (2025) 2257–2260; doi:10.1039/d4dt03314k

data_7717906
_publ_section_title
;
 An isolable boron-centered radical anion stabilized by a carbazole
 moiety.
;
_journal_issue                   6
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              2257
_journal_page_last               2260
_journal_paper_doi               10.1039/d4dt03314k
_journal_volume                  54
_journal_year                    2025
_chemical_formula_moiety         'C38 H46 B N, C20 H40 Na O10, C7 H8'
_chemical_formula_sum            'C65 H94 B N Na O10'
_chemical_formula_weight         1083.21
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2024-08-15
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_audit_update_record
;
2024-08-15 deposited with the CCDC.	2025-01-15 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.374(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.6926(6)
_cell_length_b                   20.8222(9)
_cell_length_c                   22.0394(9)
_cell_measurement_reflns_used    6671
_cell_measurement_temperature    170.01(10)
_cell_measurement_theta_max      70.4450
_cell_measurement_theta_min      4.0330
_cell_volume                     6244.8(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0793
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9990
_diffrn_measured_fraction_theta_max 0.9757
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -22.00   3.00   1.00    1.00    --    0.00 -72.00  29.00   25
  2  \w     -3.00  66.00   1.00    1.00    --    0.00  72.00 159.00   69
  3  \w     27.00 122.00   1.00    3.65    --   54.00  72.00 159.00   95
  4  \w    -11.00  80.00   1.00    3.65    --   54.00 -72.00  29.00   91
  5  \w     82.00 172.00   1.00    3.65    --  108.00  72.00 159.00   90
  6  \w     39.00 135.00   1.00    3.65    --  108.00 -72.00  29.00   96
  7  \w    -20.00  26.00   1.00    1.00    --    0.00 -77.00-150.00   46
  8  \w     -7.00  20.00   1.00    1.00    --    0.00 -77.00 -30.00   27
  9  \w     30.00 103.00   1.00    3.65    --   54.00-125.00 -60.00   73
 10  \w     30.00  55.00   1.00    3.65    --   54.00 -99.00-180.00   25
 11  \w     35.00 119.00   1.00    3.65    --   54.00  57.00-120.00   84
 12  \w    129.00 177.00   1.00    3.65    --  108.00  77.00-120.00   48
 13  \w     44.00  99.00   1.00    3.65    --  108.00 -37.00-150.00   55
 14  \w    109.00 164.00   1.00    3.65    --  108.00  77.00 120.00   55
 15  \w     63.00 106.00   1.00    3.65    --  108.00 -91.00-150.00   43
 16  \w     38.00 109.00   1.00    3.65    --  108.00-111.00  30.00   71
 17  \w     39.00  84.00   1.00    3.65    --  108.00 -91.00-180.00   45
 18  \w     62.00 145.00   1.00    3.65    --  108.00 178.00  60.00   83
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0990433000
_diffrn_orient_matrix_UB_12      0.0046237000
_diffrn_orient_matrix_UB_13      0.0266770000
_diffrn_orient_matrix_UB_21      0.0269522000
_diffrn_orient_matrix_UB_22      -0.0595963000
_diffrn_orient_matrix_UB_23      0.0399416000
_diffrn_orient_matrix_UB_31      0.0477149000
_diffrn_orient_matrix_UB_32      0.0436624000
_diffrn_orient_matrix_UB_33      0.0513493000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            27876
_diffrn_reflns_theta_full        67.07
_diffrn_reflns_theta_max         67.08
_diffrn_reflns_theta_min         3.88
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.660
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55279
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2348
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.879
_refine_diff_density_min         -0.827
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.360
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     786
_refine_ls_number_reflns         11145
_refine_ls_number_restraints     141
_refine_ls_restrained_S_all      1.370
_refine_ls_R_factor_all          0.1420
_refine_ls_R_factor_gt           0.1081
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3218
_refine_ls_wR_factor_ref         0.3747
_reflns_number_gt                7453
_reflns_number_total             11145
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d4dt03314k2.cif
_cod_data_source_block           exp_2498
_cod_depositor_comments          'Adding full bibliography for 7717906.cif.'
_cod_database_code               7717906
_chemical_oxdiff_formula         'C1 H1 N1 O1'
_diffrn_oxdiff_digest_frames
;
01fb3c275a3c59530c59325e494b93f5da0002798ec
;
_diffrn_oxdiff_digest_hkl
;
017334ca09ff3011d485c810751e6be59c113d
;
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C59-C65 = C63'-C65'
 1.53 with sigma of 0.01
 C11-C12 = C11'-C12' = C13-C14 = C13'-C14'
 1.53 with sigma of 0.01
 O2-C11 = O2-C11' = C12-O1 = C12'-O1' = C13-O1 = C13'-O1'
 1.4 with sigma of 0.01
 C65'-C62' \\sim C65'-C64'
 with sigma of 0.01
 C65-C64 \\sim C65-C60
 with sigma of 0.01
3. Rigid bond restraints
 C15, O5
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Uiso/Uaniso restraints and constraints
C59 \\sim C60 \\sim C61 \\sim C62 \\sim C63 \\sim C64 \\sim C65: within 1.7A with sigma of 0.005 and sigma for terminal atoms of 0.005
C59' \\sim C60' \\sim C61' \\sim C62' \\sim C63' \\sim C64' \\sim C65': within 1.7A with sigma of 0.005 and sigma for terminal atoms of 0.005
C11 \\sim C12 \\sim C13 \\sim C14: within 1.7A with sigma of 0.005 and sigma for terminal atoms of 0.005
C11' \\sim C12' \\sim C13' \\sim C14': within 1.7A with sigma of 0.005 and sigma for terminal atoms of 0.005
Uanis(C38) \\sim Ueq, Uanis(C39) \\sim Ueq, Uanis(C40) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C11') = Uanis(C11)
5. Others
 Sof(O1')=Sof(C11')=Sof(H1)=Sof(H11')=Sof(C12')=Sof(H12C)=Sof(H12D)=Sof(C13')=
 Sof(H13C)=Sof(H13D)=Sof(C14')=Sof(H14C)=Sof(H14D)=1-FVAR(1)
 Sof(O1)=Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(C13)=
 Sof(H13A)=Sof(H13B)=Sof(C14)=Sof(H14A)=Sof(H14B)=FVAR(1)
 Sof(C59')=Sof(H59')=Sof(C60')=Sof(H60')=Sof(C61')=Sof(H61')=Sof(C62')=
 Sof(H62')=Sof(C63')=Sof(C64')=Sof(H64')=Sof(C65')=Sof(H65D)=Sof(H65E)=
 Sof(H65F)=1-FVAR(2)
 Sof(C59)=Sof(C60)=Sof(H60)=Sof(C61)=Sof(H61)=Sof(C62)=Sof(H62)=Sof(C63)=
 Sof(H63)=Sof(C64)=Sof(H64)=Sof(C65)=Sof(H65A)=Sof(H65B)=Sof(H65C)=FVAR(2)
6.a Riding coordinates:
 C9(H9A,H9B)
6.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B),
 C7(H7A,H7B), C8(H8A,H8B), C10(H10A,H10B), C15(H15A,H15B), C16(H16A,H16B),
 C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C11(H11A,H11B),
  C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C11'(H1,H11'), C12'(H12C,
 H12D), C13'(H13C,H13D), C14'(H14C,H14D)
6.c Me refined with riding coordinates:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C38(H38A,H38B,
 H38C), C39(H39A,H39B,H39C), C40(H40A,H40B,H40C), C41(H41A,H41B,H41C), C48(H48A,
 H48B,H48C), C56(H56A,H56B,H56C), C57(H57A,H57B,H57C), C58(H58A,H58B,H58C)
6.d Aromatic/amide H refined with riding coordinates:
 C26(H26), C27(H27), C30(H30), C33(H33), C34(H34), C36(H36), C43(H43),
 C45(H45), C52(H52), C54(H54), C60(H60), C61(H61), C62(H62), C63(H63), C64(H64),
  C59'(H59'), C60'(H60'), C61'(H61'), C62'(H62'), C64'(H64')
6.e Fitted hexagon refined as free rotating group:
 C59(C60,C61,C62,C63,C64), C59'(C60',C61',C62',C63',C64')
6.f Idealised Me refined as rotating group:
 C49(H49A,H49B,H49C), C65(H65A,H65B,H65C), C65'(H65D,H65E,H65F)
;
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.462
_oxdiff_exptl_absorpt_empirical_full_min 0.640