9,9'-Bis-<i>o</i>-carboranes: synthesis and exploration of properties.
Chen, Feijing; Guo, Wenjing; Ma, Yan-Na; Chen, Xuenian; Chemical communications (Cambridge, England) 60 (2024) 614–617; doi:10.1039/d3cc05041f

data_7132439
_publ_section_title
;
 9,9'-Bis-<i>o</i>-carboranes: synthesis and exploration of properties.
;
_journal_issue                   5
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              614
_journal_page_last               617
_journal_paper_doi               10.1039/d3cc05041f
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         '2(C8 H20 N), 2(C4 H22 B19)'
_chemical_formula_sum            'C24 H84 B38 N2'
_chemical_formula_weight         811.71
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-30
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-06-07 deposited with the CCDC.	2023-12-04 downloaded from the CCDC.
;
_cell_angle_alpha                89.977(2)
_cell_angle_beta                 78.418(2)
_cell_angle_gamma                88.417(2)
_cell_formula_units_Z            2
_cell_length_a                   10.7318(3)
_cell_length_b                   13.0844(4)
_cell_length_c                   18.4673(5)
_cell_measurement_reflns_used    9400
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      71.2530
_cell_measurement_theta_min      4.8890
_cell_volume                     2539.36(13)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.976
_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    -41.00   2.00   1.00    2.39    --  -35.62  60.00  50.00   43
  2  \w    -98.00 -18.00   1.00    2.39    --  -35.62 -60.00 -88.00   80
  3  \w    -13.00  12.00   1.00    2.39    --   35.62 -60.00 -88.00   25
  4  \w     23.00 102.00   1.00    2.39    --   35.62  60.00  50.00   79
  5  \w     89.00 174.00   1.00    9.56    --  106.81  60.00  50.00   85
  6  \w     40.00 124.00   1.00    9.56    --  106.81 -60.00 -88.00   84
  7  \w    -61.00 -19.00   1.00    2.39    --  -35.62  77.00  60.00   42
  8  \w    -85.00 -41.00   1.00    2.39    --  -35.62 178.00-120.00   44
  9  \w    -13.00  25.00   1.00    2.39    --  -35.62  77.00  60.00   38
 10  \w      3.00  28.00   1.00    2.39    --   35.62  87.00-113.27   25
 11  \w    -27.00  49.00   1.00    2.39    --   35.62 -57.00-180.00   76
 12  \w     22.00  74.00   1.00    2.39    --   35.62 -99.00 -60.00   52
 13  \w     21.00  93.00   1.00    2.39    --   35.62  38.00-180.00   72
 14  \w     44.00  93.00   1.00    2.39    --   35.62-133.00 173.72   49
 15  \w     42.00 112.00   1.00    9.56    --  106.81 -61.00  60.00   70
 16  \w     40.00  69.00   1.00    9.56    --  106.81-111.00-150.00   29
 17  \w    117.00 174.00   1.00    9.56    --  106.81  61.00-150.00   57
 18  \w     42.00 107.00   1.00    9.56    --  106.81 -95.00 -60.00   65
 19  \w     51.00 108.00   1.00    9.56    --  106.81-111.00  90.00   57
 20  \w    103.00 167.00   1.00    9.56    --  106.81  77.00   0.00   64
 21  \w     37.00 126.00   1.00    9.56    --  106.81 -30.00-120.00   89
 22  \w    149.00 174.00   1.00    9.56    --  106.81  77.00-120.00   25
 23  \w    112.00 138.00   1.00    9.56    --  106.81  77.00-120.00   26
 24  \w     41.00  93.00   1.00    9.56    --  106.81-111.00  60.00   52
 25  \w     41.00 108.00   1.00    9.56    --  106.81-111.00 -90.00   67
 26  \w     73.00 108.00   1.00    9.56    --  106.81-111.00-180.00   35
 27  \w    113.00 174.00   1.00    9.56    --  106.81 111.00 -30.00   61
 28  \w     41.00 135.00   1.00    9.56    --  106.81 -15.00  30.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0447963000
_diffrn_orient_matrix_UB_12      -0.0706762000
_diffrn_orient_matrix_UB_13      0.0570270000
_diffrn_orient_matrix_UB_21      -0.0842044000
_diffrn_orient_matrix_UB_22      -0.0851571000
_diffrn_orient_matrix_UB_23      -0.0194454000
_diffrn_orient_matrix_UB_31      0.1113206000
_diffrn_orient_matrix_UB_32      -0.0403348000
_diffrn_orient_matrix_UB_33      -0.0601778000
_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  0.0404
_diffrn_reflns_av_unetI/netI     0.0575
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18413
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.310
_diffrn_reflns_theta_min         4.161
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.326
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90678
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.062
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     647
_refine_ls_number_reflns         9630
_refine_ls_number_restraints     49
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0628
_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^)+(0.0887P)^2^+1.3442P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1740
_refine_ls_wR_factor_ref         0.1828
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7921
_reflns_number_total             9630
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc05041f2.cif
_cod_data_source_block           20230530-wy_auto
_cod_depositor_comments
'Adding full bibliography for 7132433--7132440.cif.'
_cod_database_code               7132439
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'B1 N1 C1 '
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 B35-H35
 1.1 with sigma of 0.02
 C31-H31
 1 with sigma of 0.02
 C51A-H51A
 1 with sigma of 0.02
3. Rigid bond restraints
 C31, B34
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C52 \\sim C51A \\sim B50 \\sim C51: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
5. Rigid body (RIGU) restrains
 C52, C51, B50
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 C52, C51A, B50
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
6. Others
 Sof(C51A)=Sof(H51A)=1-FVAR(1)
 Sof(C51)=Sof(H51)=FVAR(1)
7.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C2(H2A,H2B), C8(H8A,H8B), C6(H6A,H6B), C13(H13A,H13B), C11(H11A,
 H11B), C17(H17A,H17B), C15(H15A,H15B)
7.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C3(H3A,H3B,H3C), C9(H9A,H9B,H9C), C7(H7A,H7B,H7C), C16(H16A,
 H16B,H16C), C14(H14A,H14B,H14C), C18(H18A,H18B,H18C), C12(H12A,H12B,H12C)
7.c Boron cage BH refined with riding coordinates:
 C23(H23), C61(H61), C19(H19), C54(H54), B34(H34), B22(H22), B64(H64),
 B39(H39), B62(H62), B21(H21), B41(H41), B24(H24), B44(H44), B60(H60), B28(H28),
  B26(H26), B43(H43), B63(H63), B38(H38), B58(H58), B65(H65), B29(H29),
 B40(H40), B57(H57), B20(H20), B53(H53), B46(H46), B30(H30), B56(H56), B27(H27),
  B45(H45), B55(H55)
;
_shelx_res_checksum              31546
_shelx_hkl_checksum              78821
_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 2.466
_oxdiff_exptl_absorpt_empirical_full_min 0.364