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_7132440
_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), C4 H22 B18'
_chemical_formula_sum            'C20 H62 B18 N2'
_chemical_formula_weight         525.29
_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             2023-06-20
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-06-21 deposited with the CCDC.	2023-12-04 downloaded from the CCDC.
;
_cell_angle_alpha                85.761(5)
_cell_angle_beta                 87.210(4)
_cell_angle_gamma                82.019(4)
_cell_formula_units_Z            4
_cell_length_a                   11.2612(5)
_cell_length_b                   17.2885(10)
_cell_length_c                   18.0579(11)
_cell_measurement_reflns_used    5722
_cell_measurement_temperature    297
_cell_measurement_theta_max      69.4130
_cell_measurement_theta_min      3.9430
_cell_volume                     3469.5(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (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  (Sheldrick, 2015)'
_diffrn_ambient_temperature      297
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.980
_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   -102.00 -15.60   0.80    4.00    --  -33.50 -57.00 150.00  108
  2  \w    -90.00  -4.40   0.80    4.00    --  -33.50 130.00 -21.00  107
  3  \w   -108.00 -36.00   0.80    4.00    --  -33.50 178.00-120.00   90
  4  \w   -102.00 -15.60   0.80    4.00    --  -33.50 -57.00 -90.00  108
  5  \w   -108.00 -36.00   0.80    4.00    --  -33.50 178.00   0.00   90
  6  \w   -102.00 -15.60   0.80    4.00    --  -33.50 -57.00-120.00  108
  7  \w    -34.00  34.00   0.80    4.00    --  -33.50  57.00 -60.00   85
  8  \w    -57.00  35.00   0.80    4.00    --  -33.50  19.00  60.00  115
  9  \w     33.00  92.20   0.80    4.00    --   36.47-130.00 -93.00   74
 10  \w     90.00 169.20   0.80   17.50    --  108.00  45.00 -60.00   99
 11  \w     79.00 103.80   0.80   17.50    --  108.00 -94.00 -60.00   31
 12  \w     52.00 107.20   0.80   17.50    --  108.00-111.00  60.00   69
 13  \w     42.00 104.40   0.80   17.50    --  108.00 -94.00 120.00   78
 14  \w     53.00 126.60   0.80   17.50    --  108.00 -30.00 -90.00   92
 15  \w     74.00 108.40   0.80   17.50    --  108.00-111.00-150.00   43
 16  \w    129.00 176.20   0.80   17.50    --  108.00  45.00 -30.00   59
 17  \w     39.00 121.40   0.80   17.50    --  108.00 -30.00   0.00  103
 18  \w     47.00  82.20   0.80   17.50    --  108.00 -61.00  30.00   44
 19  \w     77.00 105.80   0.80   17.50    --  108.00-111.00 -90.00   36
 20  \w     44.00  70.40   0.80   17.50    --  108.00-111.00 -90.00   33
 21  \w     42.00 118.00   0.80   17.50    --  108.00 -61.00-120.00   95
 22  \w     63.00 127.00   0.80   17.50    --  108.00 -61.00 150.00   80
 23  \w     93.00 120.20   0.80   17.50    --  108.00  45.00 -30.00   34
 24  \w     46.00 119.60   0.80   17.50    --  108.00 -45.00  90.00   92
 25  \w     68.00 164.00   0.80   17.50    --  108.00  15.00 -90.00  120
 26  \w    105.00 133.00   0.80   17.50    --  108.00 -77.00 -90.00   35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0247939000
_diffrn_orient_matrix_UB_12      -0.0666170000
_diffrn_orient_matrix_UB_13      -0.0467579000
_diffrn_orient_matrix_UB_21      -0.0184499000
_diffrn_orient_matrix_UB_22      -0.0517500000
_diffrn_orient_matrix_UB_23      0.0716804000
_diffrn_orient_matrix_UB_31      -0.1347465000
_diffrn_orient_matrix_UB_32      0.0319075000
_diffrn_orient_matrix_UB_33      0.0022056000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            25502
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.414
_diffrn_reflns_theta_min         3.444
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.338
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96723
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.006
_exptl_crystal_description       block
_exptl_crystal_F_000             1144
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.536
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     903
_refine_ls_number_reflns         12998
_refine_ls_number_restraints     69
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1235
_refine_ls_R_factor_gt           0.0877
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1784P)^2^+0.2996P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2596
_refine_ls_wR_factor_ref         0.3026
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8074
_reflns_number_total             12998
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc05041f2.cif
_cod_data_source_block           202305122_auto
_cod_depositor_comments
'Adding full bibliography for 7132433--7132440.cif.'
_cod_database_code               7132440
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C20H20N2O1B7
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All H(H) groups, All B(H) groups, All B(H,H) groups, All C(H) groups, All
  C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups
2. Restrained distances
 C3F-C4F
 1.54 with sigma of 0.02
 C1F'-C7F'
 2.2 with sigma of 0.02
 N1F-C7F'
 1.54 with sigma of 0.02
 H4A'-C4A' = C4A-H4AA
 0.96 with sigma of 0.02
 H4BB-C4B = C4B'-H4B'
 0.96 with sigma of 0.02
 C2B-H2BA = C1B'-H1BA
 0.96 with sigma of 0.02
 B3A-H3AA
 1.1 with sigma of 0.02
 H2A-C2A = H1A-C1A
 0.96 with sigma of 0.02
 B2B-H1B' = H1B'-B3B
 1.1 with sigma of 0.02
 B11B-H11A = H11A-B12B
 1.1 with sigma of 0.02
 B2A-H2AB = H2AB-B3A
 1.1 with sigma of 0.02
 B11A-H11D = H11D-B12A
 1.1 with sigma of 0.02
 B14A-H13D = H13D-B13A
 1.1 with sigma of 0.02
 B13B-H13A = H13A-B14B
 1.1 with sigma of 0.02
 B5B-H4BA = H4BA-B4B
 1.1 with sigma of 0.02
3. Rigid bond restraints
 C1B, B4B, B5B, B9B, B8B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 B11A, B12A, B16A, B17A, C3A, C4A'
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Uiso/Uaniso restraints and constraints
C4F \\sim C3F' \\sim C3F: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
5. Others
 Sof(H2DD)=Sof(H2DE)=Sof(H2DF)=Sof(H4DD)=Sof(H4DE)=Sof(H4DF)=Sof(H6DD)=
 Sof(H6DE)=Sof(H6DF)=Sof(H8DD)=Sof(H8DE)=Sof(H8DF)=Sof(C1D')=Sof(H1DA)=
 Sof(H1DB)=Sof(C3D')=Sof(H3DA)=Sof(H3DB)=Sof(C5D')=Sof(H5DA)=Sof(H5DB)=
 Sof(C7D')=Sof(H7DA)=Sof(H7DB)=1-FVAR(1)
 Sof(H2DA)=Sof(H2DB)=Sof(H2DC)=Sof(H4DA)=Sof(H4DB)=Sof(H4DC)=Sof(H6DA)=
 Sof(H6DB)=Sof(H6DC)=Sof(H8DA)=Sof(H8DB)=Sof(H8DC)=Sof(C1D)=Sof(H1DC)=Sof(H1DD)=
 Sof(C3D)=Sof(H3DC)=Sof(H3DD)=Sof(C5D)=Sof(H5DC)=Sof(H5DD)=Sof(C7D)=Sof(H7DC)=
 Sof(H7DD)=FVAR(1)
 Sof(H2FD)=Sof(H2FE)=Sof(H2FF)=Sof(H4FD)=Sof(H4FE)=Sof(H4FF)=Sof(H6FD)=
 Sof(H6FE)=Sof(H6FF)=Sof(H8FD)=Sof(H8FE)=Sof(H8FF)=Sof(C7F')=Sof(H7FA)=
 Sof(H7FB)=Sof(C5F')=Sof(H5FA)=Sof(H5FB)=Sof(C3F')=Sof(H3FA)=Sof(H3FB)=
 Sof(C1F')=Sof(H1FA)=Sof(H1FB)=1-FVAR(2)
 Sof(H2FA)=Sof(H2FB)=Sof(H2FC)=Sof(H4FA)=Sof(H4FB)=Sof(H4FC)=Sof(H6FA)=
 Sof(H6FB)=Sof(H6FC)=Sof(H8FA)=Sof(H8FB)=Sof(H8FC)=Sof(C1F)=Sof(H1FC)=Sof(H1FD)=
 Sof(C3F)=Sof(H3FC)=Sof(H3FD)=Sof(C5F)=Sof(H5FC)=Sof(H5FD)=Sof(C7F)=Sof(H7FC)=
 Sof(H7FD)=FVAR(2)
 Sof(C4A')=Sof(H10D)=Sof(H13D)=Sof(H4A')=1-FVAR(3)
 Sof(H10C)=Sof(H11D)=Sof(H4AA)=Sof(C4A)=FVAR(3)
 Sof(C4B')=Sof(H4B')=Sof(H10A)=Sof(H13A)=1-FVAR(4)
 Sof(H10B)=Sof(H11A)=Sof(C4B)=Sof(H4BB)=FVAR(4)
 Sof(C1B')=Sof(H1BA)=Sof(H1BC)=Sof(H4BA)=1-FVAR(5)
 Sof(H1BB)=Sof(H1B')=Sof(C2B)=Sof(H2BA)=FVAR(5)
6.a Riding coordinates:
 C2D(H2DA,H2DB,H2DC), C2D(H2DD,H2DE,H2DF), C6D(H6DA,H6DB,H6DC), C6D(H6DD,H6DE,
 H6DF), C2F(H2FA,H2FB,H2FC), C2F(H2FD,H2FE,H2FF), C4F(H4FA,H4FB,H4FC), C4F(H4FD,
 H4FE,H4FF), C3B(H3B), C4B'(H4B')
6.b Secondary CH2 refined with riding coordinates:
 C1C(H1CA,H1CB), C3C(H3CA,H3CB), C5C(H5CA,H5CB), C7C(H7CA,H7CB), C1D'(H1DA,
 H1DB), C3D'(H3DA,H3DB), C5D'(H5DA,H5DB), C7D'(H7DA,H7DB), C1E(H1EA,H1EB),
 C3E(H3EA,H3EB), C5E(H5EA,H5EB), C7E(H7EA,H7EB), C7F'(H7FA,H7FB), C5F'(H5FA,
 H5FB), C3F'(H3FA,H3FB), C1F'(H1FA,H1FB), C1D(H1DC,H1DD), C1F(H1FC,H1FD),
 C3D(H3DC,H3DD), C3F(H3FC,H3FD), C5D(H5DC,H5DD), C5F(H5FC,H5FD), C7D(H7DC,H7DD),
  C7F(H7FC,H7FD)
6.c Idealised Me refined as rotating group:
 C2C(H2CA,H2CB,H2CC), C4C(H4CA,H4CB,H4CC), C6C(H6CA,H6CB,H6CC), C8C(H8CA,H8CB,
 H8CC), C4D(H4DA,H4DB,H4DC), C4D(H4DD,H4DE,H4DF), C8D(H8DA,H8DB,H8DC), C8D(H8DD,
 H8DE,H8DF), C2E(H2EA,H2EB,H2EC), C4E(H4EA,H4EB,H4EC), C6E(H6EA,H6EB,H6EC),
 C8E(H8EA,H8EB,H8EC), C6F(H6FA,H6FB,H6FC), C6F(H6FD,H6FE,H6FF), C8F(H8FA,H8FB,
 H8FC), C8F(H8FD,H8FE,H8FF)
6.d Boron cage BH refined with riding coordinates:
 B4A(H4A), B5A(H5A), B7A(H7A), B8A(H8A), B9A(H9A), B10A(H10C), B10A(H10D),
 B11A(H11C), B12A(H12A), B13A(H13C), B14A(H14A), B16A(H16A), B17A(H17A),
 B18A(H18A), B1B(H1BB), B1B(H1BC), B2B(H2B), B3B(H3BA), B4B(H4B), B5B(H5B),
 B7B(H7B), B8B(H8B), B9B(H9B), B10B(H10B), B10B(H10A), B11B(H11B), B12B(H12B),
 B13B(H13B), B14B(H14B), B16B(H16B), B17B(H17B), B18B(H18B)
;
_shelx_res_checksum              815
_shelx_hkl_checksum              95851
_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 1.161
_oxdiff_exptl_absorpt_empirical_full_min 0.934