Isolation of the elusive bisbenzimidazole Bbim3−˙ radical anion and its employment in a metal complex
Benner, Florian; Demir, Selvan; Chemical Science  (2022) –; doi:10.1039/D1SC07245E

data_1566800
_publ_section_title
;
 Isolation of the elusive bisbenzimidazole Bbim3&#x2212;&#x02D9; radical
 anion and its employment in a metal complex
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC07245E
_journal_year                    2022
_chemical_formula_moiety         'C54 H68 N4 Y2, C18 H36 K N2 O6, 3(C4 H8 O)'
_chemical_formula_sum            'C84 H128 K N6 O9 Y2'
_chemical_formula_weight         1582.84
_chemical_properties_physical
Air-sensitive,Moisture-sensitive,Heat-sensitive,Oxygen-sensitive
_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     dual
_audit_creation_date             2021-11-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-11-20 deposited with the CCDC.	2022-04-05 downloaded from the CCDC.
;
_cell_angle_alpha                86.907(2)
_cell_angle_beta                 78.0500(10)
_cell_angle_gamma                76.349(2)
_cell_formula_units_Z            2
_cell_length_a                   13.0300(2)
_cell_length_b                   18.0681(4)
_cell_length_c                   18.3710(3)
_cell_measurement_reflns_used    32015
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      30.9570
_cell_measurement_theta_min      2.2890
_cell_volume                     4111.72(13)
_computing_cell_refinement       'CrysAlisPro 1.171.41.96a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.96a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.96a (Rigaku OD, 2021)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.818
_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     -7.00  18.00   0.50   60.00    --    4.87  37.00  60.00   50
  2  \w     -6.00  42.00   0.50   60.00    --    4.87  37.00   0.00   96
  3  \w     32.00  57.00   0.50   60.00    --   -5.34  19.00 -60.00   50
  4  \w     -6.00  42.00   0.50   60.00    --    4.87  37.00-180.00   96
  5  \w    -28.00  -2.00   0.50   60.00    --   -5.34  77.00-120.00   52
  6  \w    -10.00  29.00   0.50   60.00    --   -5.34  19.00 -60.00   78
  7  \w      0.00  25.00   0.50   60.00    --    4.87 -77.00-120.00   50
  8  \w    -57.00  24.00   0.50   60.00    --    4.87 -69.00  41.00  162
  9  \w    -42.00 -15.00   0.50   60.00    --    4.87 -37.00  90.00   54
 10  \w    -52.00   3.00   0.50   60.00    --    4.87 -19.00 120.00  110
 11  \w     -6.00  41.00   0.50   60.00    --    4.87  37.00  90.00   94
 12  \w    -10.00  76.00   0.50   60.00    --    4.87  69.00 174.00  172
 13  \w    -28.00  -3.00   0.50   60.00    --   -5.34  77.00 150.00   50
 14  \w    -28.00  -3.00   0.50   60.00    --   -5.34  77.00  60.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0169512000
_diffrn_orient_matrix_UB_12      0.0344114000
_diffrn_orient_matrix_UB_13      -0.0095415000
_diffrn_orient_matrix_UB_21      0.0288975000
_diffrn_orient_matrix_UB_22      -0.0060772000
_diffrn_orient_matrix_UB_23      0.0293668000
_diffrn_orient_matrix_UB_31      0.0463333000
_diffrn_orient_matrix_UB_32      -0.0202729000
_diffrn_orient_matrix_UB_33      -0.0245782000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.818
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            82579
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.818
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.927
_diffrn_reflns_theta_min         2.174
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.513
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.604
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.96a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dull dark green'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_description       block
_exptl_crystal_F_000             1686
_exptl_crystal_size_max          0.145
_exptl_crystal_size_mid          0.119
_exptl_crystal_size_min          0.084
_refine_diff_density_max         1.597
_refine_diff_density_min         -0.515
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     966
_refine_ls_number_reflns         21330
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0458
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0569P)^2^+2.7355P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1102
_reflns_Friedel_coverage         0.000
_reflns_number_gt                17056
_reflns_number_total             21330
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc07245e2.cif
_cod_data_source_block           fb439_k2_110720_1
_cod_database_code               1566800
_shelxl_version_number           2013-3
_chemical_oxdiff_formula         C72H104KN6O6Y2
_shelx_estimated_absorpt_t_max   0.883
_shelx_estimated_absorpt_t_min   0.810
_diffrn_oxdiff_digest_frames
;
01154e664b4639008d1ce80226747c663d01164c8b9
;
_diffrn_oxdiff_digest_hkl
;
01dc744cb288d2b89fd26bd950878f19443d48
;
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C77, O8, C80, C79, C78
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Others
 Fixed Sof: H82C(0.5) H82D(0.5) H82A(0.5) H82B(0.5) H81A(0.5) H81B(0.5)
 H81C(0.5) H81D(0.5) C85(0.6) H85A(0.6) H85B(0.6) O9(0.5) O10(0.5) C86(0.6)
 H86A(0.6) H86B(0.6) C84(0.4) H84A(0.4) H84B(0.4) C83(0.4) H83A(0.4) H83B(0.4)
4.a Secondary CH2 refined with riding coordinates:
 C64(H64A,H64B), C60(H60A,H60B), C65(H65A,H65B), C66(H66A,H66B), C63(H63A,
 H63B), C61(H61A,H61B), C55(H55A,H55B), C68(H68A,H68B), C58(H58A,H58B),
 C62(H62A,H62B), C56(H56A,H56B), C76(H76A,H76B), C75(H75A,H75B), C69(H69A,H69B),
  C67(H67A,H67B), C59(H59A,H59B), C70(H70A,H70B), C71(H71A,H71B), C72(H72A,
 H72B), C74(H74A,H74B), C57(H57A,H57B), C73(H73A,H73B), C82(H82C,H82D),
 C82(H82A,H82B), C81(H81A,H81B), C81(H81C,H81D), C85(H85A,H85B), C86(H86A,H86B),
  C84(H84A,H84B), C83(H83A,H83B), C77(H77A,H77B), C80(H80A,H80B), C78(H78A,
 H78B), C79(H79A,H79B)
4.b Aromatic/amide H refined with riding coordinates:
 C53(H53), C46(H46), C52(H52), C45(H45), C50(H50), C43(H43), C51(H51), C44(H44)
4.c Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C), C26(H26A,H26B,H26C), C30(H30A,H30B,H30C), C27(H27A,H27B,
 H27C), C40(H40A,H40B,H40C), C28(H28A,H28B,H28C), C37(H37A,H37B,H37C), C39(H39A,
 H39B,H39C), C10(H10A,H10B,H10C), C6(H6A,H6B,H6C), C36(H36A,H36B,H36C),
 C29(H29A,H29B,H29C), C9(H9A,H9B,H9C), C16(H16A,H16B,H16C), C3AA(H3AA,H3AB,
 H3AC), C17(H17A,H17B,H17C), C7(H7A,H7B,H7C), C18(H18A,H18B,H18C), C19(H19A,
 H19B,H19C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              66697
_shelx_hkl_checksum              21904
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.267
_oxdiff_exptl_absorpt_empirical_full_min 0.835