NHC-BH<sub>2</sub>-C<sub>60</sub>H: synthesis, characterization and electrochemical properties of the N-heterocyclic-carbene-stabilized fullerene-borane complex.
Yuan, Sheng-Hu; Ma, Shu-Chao; Wu, Jian; Zheng, Xiu-Ying; Xuan, Jun; Li, Fei; Chemical communications (Cambridge, England) 61 (2025) 528–531; doi:10.1039/d4cc04866k

data_7134011
_publ_section_title
;
 NHC-BH<sub>2</sub>-C<sub>60</sub>H: synthesis, characterization and
 electrochemical properties of the N-heterocyclic-carbene-stabilized
 fullerene-borane complex.
;
_journal_issue                   3
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              528
_journal_page_last               531
_journal_paper_doi               10.1039/d4cc04866k
_journal_volume                  61
_journal_year                    2025
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C65 H11 B N2, C0.5 S'
_chemical_formula_sum            'C65.5 H11 B N2 S'
_chemical_formula_weight         868.63
_space_group_crystal_system      tetragonal
_space_group_IT_number           96
_space_group_name_Hall           'P 4nw 2abw'
_space_group_name_H-M_alt        'P 43 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2024-11-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-11-20 deposited with the CCDC.	2024-11-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.8769(2)
_cell_length_b                   13.8769(2)
_cell_length_c                   35.5657(12)
_cell_measurement_reflns_used    4301
_cell_measurement_temperature    120
_cell_measurement_theta_max      76.3620
_cell_measurement_theta_min      3.4230
_cell_volume                     6848.8(3)
_computing_cell_refinement       'CrysAlisPro 1.171.43.100a (Rigaku OD, 2023)'
_computing_data_collection
'CrysAlisPro system (CCD 42.93a 64-bit (release 05-06-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.100a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      120
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.963
_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     47.00 103.00   0.50    3.00    --   49.58-138.00 114.00  112
  2  \w   -121.00 -32.00   0.50   12.00    -- -104.50 138.00 176.00  178
  3  \w     96.00 154.00   0.50   12.00    --  106.85  98.00 -71.00  116
  4  \w    -18.00  13.00   0.50    3.00    --  -49.58  19.00-150.00   62
  5  \w     75.00 110.00   0.50    3.00    --   49.58 138.00 176.00   70
  6  \w    -62.00 -33.00   0.50   12.00    -- -104.50  57.00 120.00   58
  7  \w     43.00  97.00   0.50   12.00    --  106.85 -99.00 150.00  108
  8  \w     39.00 109.00   0.50   12.00    --  106.85-125.00 150.00  140
  9  \w    129.00 177.00   0.50   12.00    --  106.85  19.00 -90.00   96
 10  \w     41.00  68.00   0.50   12.00    --  106.85 -57.00-120.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0191921000
_diffrn_orient_matrix_UB_12      -0.0589899000
_diffrn_orient_matrix_UB_13      0.0359293000
_diffrn_orient_matrix_UB_21      -0.0319911000
_diffrn_orient_matrix_UB_22      -0.0863023000
_diffrn_orient_matrix_UB_23      -0.0241305000
_diffrn_orient_matrix_UB_31      0.1046542000
_diffrn_orient_matrix_UB_32      -0.0374281000
_diffrn_orient_matrix_UB_33      -0.0007753000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.2070
_diffrn_reflns_av_unetI/netI     0.1593
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            20418
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.403
_diffrn_reflns_theta_min         3.419
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.314
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.100a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.685
_exptl_crystal_description       block
_exptl_crystal_F_000             3512
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.029
_refine_diff_density_min         -0.919
_refine_diff_density_rms         0.209
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.48(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     630
_refine_ls_number_reflns         6942
_refine_ls_number_restraints     402
_refine_ls_restrained_S_all      1.175
_refine_ls_R_factor_all          0.1970
_refine_ls_R_factor_gt           0.1632
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.3500P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4182
_refine_ls_wR_factor_ref         0.4511
_reflns_Friedel_coverage         0.692
_reflns_Friedel_fraction_full    0.978
_reflns_Friedel_fraction_max     0.913
_reflns_number_gt                5059
_reflns_number_total             6942
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc04866k2.cif
_cod_data_source_block           64_auto-2
_cod_depositor_comments          'Adding full bibliography for 7134011.cif.'
_cod_original_cell_volume        6848.9(3)
_cod_original_formula_sum        'C65.50 H11 B N2 S'
_cod_database_code               7134011
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H B N S'
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.962
_reflns_odcompleteness_completeness 99.14
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.52(10)
 0.48(10)
2. Fixed Uiso
 At 1.2 times of:
  All B(H,H) groups, All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(C1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C4) \\sim
Ueq, Uanis(C5) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C8)
\\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C11) \\sim Ueq,
Uanis(C12) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C15)
\\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C18) \\sim Ueq,
Uanis(C19) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C22)
\\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C25) \\sim Ueq,
Uanis(C26) \\sim Ueq, Uanis(C27) \\sim Ueq, Uanis(C28) \\sim Ueq, Uanis(C29)
\\sim Ueq, Uanis(C30) \\sim Ueq, Uanis(C31) \\sim Ueq, Uanis(C32) \\sim Ueq,
Uanis(C33) \\sim Ueq, Uanis(C34) \\sim Ueq, Uanis(C35) \\sim Ueq, Uanis(C36)
\\sim Ueq, Uanis(C37) \\sim Ueq, Uanis(C38) \\sim Ueq, Uanis(C39) \\sim Ueq,
Uanis(C40) \\sim Ueq, Uanis(C41) \\sim Ueq, Uanis(C42) \\sim Ueq, Uanis(C43)
\\sim Ueq, Uanis(C44) \\sim Ueq, Uanis(C45) \\sim Ueq, Uanis(C46) \\sim Ueq,
Uanis(C47) \\sim Ueq, Uanis(C48) \\sim Ueq, Uanis(C49) \\sim Ueq, Uanis(C50)
\\sim Ueq, Uanis(C51) \\sim Ueq, Uanis(C52) \\sim Ueq, Uanis(C53) \\sim Ueq,
Uanis(C54) \\sim Ueq, Uanis(C55) \\sim Ueq, Uanis(C56) \\sim Ueq, Uanis(C57)
\\sim Ueq, Uanis(C58) \\sim Ueq, Uanis(C59) \\sim Ueq, Uanis(C60) \\sim Ueq,
Uanis(C61) \\sim Ueq, Uanis(C62) \\sim Ueq, Uanis(C63) \\sim Ueq, Uanis(C64)
\\sim Ueq, Uanis(C65) \\sim Ueq, Uanis(C66) \\sim Ueq, Uanis(N1) \\sim Ueq:
with sigma of 0.005 and sigma for terminal atoms of 0.005
Uanis(C38) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C12)
\\sim Ueq, Uanis(C39) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C45) \\sim Ueq,
Uanis(C24) \\sim Ueq, Uanis(C32) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
4.a Ternary CH refined with riding coordinates:
 C46(H46)
4.b Secondary CH2 refined with riding coordinates:
 B1(H1A,H1B)
4.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C27(H27)
4.d Idealised Me refined as rotating group:
 C35(H35A,H35B,H35C), C56(H56A,H56B,H56C)
;
_shelx_res_checksum              8963
_shelx_hkl_checksum              71838
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.881
_oxdiff_exptl_absorpt_empirical_full_min 0.070