[closo-B10H8-1,10-(COOH)2]2-: A building block for functional materials?
Kapuscinski, Szymon; Hietsoi, Oleksandr; Pietrzak, Anna; Friedli, Andrienne C.; Kaszynski, Piotr; Chemical Communications  (2022) –; doi:10.1039/D1CC06485A

data_7129387
_publ_section_title
;
 [closo-B10H8-1,10-(COOH)2]2-: A building block for functional materials?
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC06485A
_journal_year                    2022
_chemical_formula_moiety         'C6 H18 B10 O4, 2(C8 H20 N)'
_chemical_formula_sum            'C22 H58 B10 N2 O4'
_chemical_formula_weight         522.80
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-24
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_audit_update_record
;
2021-05-05 deposited with the CCDC.	2021-12-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.1637(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.45359(6)
_cell_length_b                   10.53655(5)
_cell_length_c                   18.37001(7)
_cell_measurement_reflns_used    58909
_cell_measurement_temperature    100.00(11)
_cell_measurement_theta_max      76.3070
_cell_measurement_theta_min      2.6900
_cell_volume                     3159.84(2)
_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    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_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    -66.00   1.00   0.50   10.00    --    0.00  -8.00  52.63  134
  2  \w    -49.00 -17.00   0.50   10.00    --    6.00 133.00 139.59   64
  3  \w     -7.00  18.00   0.50   10.00    --   26.00  96.00  15.42   50
  4  \w      4.00  30.00   0.50   10.00    --   30.00  85.00 -92.91   52
  5  \w    -22.00   4.00   0.50   10.00    --   34.00 -50.00-153.92   52
  6  \w      7.00  38.00   0.50   10.00    --   34.00 -50.00-153.92   62
  7  \w     13.00  38.00   0.50   10.00    --   38.00  82.00-126.98   50
  8  \w     16.00  41.00   0.50   10.00    --   38.00  78.00-171.54   50
  9  \w     13.00  40.00   0.50   10.00    --   38.00  82.00 145.44   54
 10  \w     13.00  38.00   0.50   10.00    --   38.00  82.00  64.00   50
 11  \w     14.00  42.00   0.50   10.00    --   38.00  81.00 112.06   56
 12  \w     13.00  38.00   0.50   10.00    --   38.00  82.00  -3.18   50
 13  \w     14.00  39.00   0.50   10.00    --   38.00  81.00 -59.53   50
 14  \w    -20.00  44.00   0.50   10.00    --   42.00 -41.00 137.31  128
 15  \w    -18.00  48.00   0.50   10.00    --   42.00 -60.00 -45.28  132
 16  \w     30.00  72.00   0.50   10.00    --   50.00  74.00  42.92   84
 17  \w     30.00  59.00   0.50   10.00    --   50.00  74.00 -11.27   58
 18  \w     32.00  58.00   0.50   10.00    --   50.00  72.00 -70.65   52
 19  \w     34.00  59.00   0.50   10.00    --   54.00  74.00 -47.34   50
 20  \w     34.00  59.00   0.50   10.00    --   54.00  74.00 138.45   50
 21  \w     34.00  60.00   0.50   10.00    --   54.00  74.00-145.55   52
 22  \w     -8.00  57.00   0.50   10.00    --   54.00 -47.00 -28.84  130
 23  \w     90.00 116.00   0.50   10.00    --   54.00  74.00 -47.34   52
 24  \w     38.00  64.00   0.50   10.00    --   58.00  74.00  79.13   52
 25  \w     40.00  65.00   0.50   10.00    --   58.00  72.00 160.89   50
 26  \w     38.00  63.00   0.50   10.00    --   58.00  74.00-179.01   50
 27  \w     38.00  64.00   0.50   10.00    --   58.00  74.00 104.22   52
 28  \w     90.00 117.00   0.50   10.00    --   58.00  74.00 104.22   54
 29  \w     38.00  68.00   0.50   10.00    --   58.00  74.00  -1.52   60
 30  \w     40.00  91.00   0.50   10.00    --   58.00  73.00 -94.76  102
 31  \w     42.00  77.00   0.50   10.00    --   62.00  74.00-129.60   70
 32  \w     44.00  79.00   0.50   10.00    --   62.00  72.00-155.31   70
 33  \w     42.00  69.00   0.50   10.00    --   62.00  74.00  50.84   54
 34  \w     82.00 108.00   0.50   10.00    --   62.00  74.00-129.60   52
 35  \w     54.00  89.00   0.50   10.00    --   66.00  65.00 134.77   70
 36  \w     48.00  73.00   0.50   10.00    --   66.00  73.00 -31.35   50
 37  \w     99.00 130.00   0.50   10.00    --   70.00  73.00-109.28   62
 38  \w     52.00  81.00   0.50   10.00    --   70.00  73.00-109.28   58
 39  \w     52.00  85.00   0.50   10.00    --   70.00  72.00 -70.62   66
 40  \w     53.00  78.00   0.50   10.00    --   70.00  69.00 167.37   50
 41  \w    106.00 132.00   0.50   10.00    --   70.00  72.00 -70.62   52
 42  \w     57.00  83.00   0.50   10.00    --   74.00  72.00 -33.56   52
 43  \w     58.00  86.00   0.50   10.00    --   74.00  70.00 176.47   56
 44  \w     60.00  87.00   0.50   10.00    --   74.00  68.00 108.09   54
 45  \w     61.00  87.00   0.50   10.00    --   78.00  73.00  62.47   52
 46  \w     66.00  91.00   0.50   10.00    --   78.00  62.00 -42.04   50
 47  \w     63.00  88.00   0.50   10.00    --   78.00  67.00 -10.09   50
 48  \w     67.00  99.00   0.50   10.00    --   78.00  62.00 -98.44   64
 49  \w     61.00  87.00   0.50   10.00    --   78.00  72.00  -1.30   52
 50  \w    112.00 138.00   0.50   10.00    --   78.00  73.00  62.47   52
 51  \w     73.00  99.00   0.50   10.00    --   82.00  56.00  95.38   52
 52  \w     80.00 106.00   0.50   10.00    --   86.00  53.00  66.45   52
 53  \w    108.00 145.00   0.50   10.00    --   86.00  74.00  13.20   74
 54  \w     66.00 102.00   0.50   10.00    --   86.00  74.00  13.20   72
 55  \w     70.00 130.00   0.50   10.00    --   86.00  68.00  -9.97  120
 56  \w    132.00 162.00   0.50   10.00    --  102.85  70.00 104.54   60
 57  \w     92.00 165.00   0.50   10.00    --  102.85  61.00-120.00  146
 58  \w     86.00 117.00   0.50   10.00    --  102.85  70.00 104.54   62
 59  \w     91.00 162.00   0.50   10.00    --  102.85  61.00 -60.00  142
 60  \w     46.00 121.00   0.50   10.00    --  102.85-137.00 179.00  150
 61  \w     91.00 118.00   0.50   10.00    --  102.85  61.00 150.00   54
 62  \w     92.00 165.00   0.50   10.00    --  102.85  61.00-150.00  146
 63  \w     93.00 165.00   0.50   10.00    --  102.85  61.00 -30.00  144
 64  \w     91.00 161.00   0.50   10.00    --  102.85  61.00 -90.00  140
 65  \w     80.00 111.00   0.50   10.00    --  102.85-125.00-120.00   62
 66  \w     41.00  66.00   0.50   10.00    --  102.85-125.00-120.00   50
 67  \w     57.00 115.00   0.50   10.00    --  102.85 -61.00   0.00  116
 68  \w     83.00 143.00   0.50   10.00    --  102.85  74.00-177.55  120
 69  \w    129.00 165.00   0.50   10.00    --  102.85  45.00 150.00   72
 70  \w    100.00 126.00   0.50   10.00    --  102.85  45.00 150.00   52
 71  \w     40.00  98.00   0.50   10.00    --  102.85-125.00 -30.00  116
 72  \w     92.00 118.00   0.50   10.00    --  102.85  61.00  60.00   52
 73  \w     50.00  99.00   0.50   10.00    --  102.85 -45.00 120.00   98
 74  \w     40.00  99.00   0.50   10.00    --  102.85 -45.00 -60.00  118
 75  \w     41.00  98.00   0.50   10.00    --  102.85 -45.00-180.00  114
 76  \w    133.00 160.00   0.50   10.00    --  102.85  61.00  90.00   54
 77  \w     91.00 117.00   0.50   10.00    --  102.85  61.00  90.00   52
 78  \w    109.00 154.00   0.50   10.00    --  102.85 125.00 -90.00   90
 79  \w     51.00 106.00   0.50   10.00    --  102.85 -95.00 -90.00  110
 80  \w     41.00 114.00   0.50   10.00    --  102.85 -77.00 -30.00  146
 81  \w     44.00  89.00   0.50   10.00    --  102.85 -30.00   0.00   90
 82  \w     91.00 163.00   0.50   10.00    --  102.85  61.00  30.00  144
 83  \w     75.00 106.00   0.50   10.00    --  102.85 -61.00 150.00   62
 84  \w    134.00 165.00   0.50   10.00    --  102.85  61.00-180.00   62
 85  \w    127.00 165.00   0.50   10.00    --  102.85  61.00  60.00   76
 86  \w     91.00 116.00   0.50   10.00    --  102.85  61.00-180.00   50
 87  \w     43.00  68.00   0.50   10.00    --  102.85 -61.00 150.00   50
 88  \w     80.00 106.00   0.50   10.00    --  102.85 -95.00 120.00   52
 89  \w     37.00  62.00   0.50   10.00    --  102.85 -95.00 120.00   50
 90  \w    137.00 164.00   0.50   10.00    --  102.85  61.00 120.00   54
 91  \w     42.00  75.00   0.50   10.00    --  102.85 -95.00 -30.00   66
 92  \w     79.00 105.00   0.50   10.00    --  102.85 -95.00 -30.00   52
 93  \w     93.00 119.00   0.50   10.00    --  102.85  61.00 120.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0369512000
_diffrn_orient_matrix_UB_12      -0.0072535000
_diffrn_orient_matrix_UB_13      -0.0729449000
_diffrn_orient_matrix_UB_21      -0.0859588000
_diffrn_orient_matrix_UB_22      0.0180115000
_diffrn_orient_matrix_UB_23      -0.0426883000
_diffrn_orient_matrix_UB_31      0.0124742000
_diffrn_orient_matrix_UB_32      0.1448565000
_diffrn_orient_matrix_UB_33      0.0016983000
_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  0.0240
_diffrn_reflns_av_unetI/netI     0.0078
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            73357
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.570
_diffrn_reflns_theta_min         2.707
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.505
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73227
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.099
_exptl_crystal_description       block
_exptl_crystal_F_000             1144
_exptl_crystal_preparation       'isolated from EtOH/DCM'
_exptl_crystal_recrystallization_method 'isolated from EtOH/DCM'
_exptl_crystal_size_max          0.332
_exptl_crystal_size_mid          0.274
_exptl_crystal_size_min          0.168
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         6577
_refine_ls_number_restraints     97
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0539
_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^)+(0.0709P)^2^+1.6450P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1446
_refine_ls_wR_factor_ref         0.1450
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6407
_reflns_number_total             6577
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc06485a2.cif
_cod_data_source_block           sk_012_d
_cod_database_code               7129387
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         C22H54B10N2O4
_shelx_estimated_absorpt_t_max   0.920
_shelx_estimated_absorpt_t_min   0.850
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N2-C17 \\sim N2-C17A
 with sigma of 0.02
 C17-C18 \\sim C17A-C18A
 with sigma of 0.02
 N2-C18 \\sim N2-C18A
 with sigma of 0.04
 N2-C15 \\sim N2-C15A
 with sigma of 0.02
 C15-C16 \\sim C15A-C16A
 with sigma of 0.02
 N2-C16 \\sim N2-C16A
 with sigma of 0.04
 O1-C1 \\sim O1A-C1
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C17 \\sim C18 \\sim C17A \\sim C18A: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
C15 \\sim C16 \\sim C15A \\sim C16A: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
O1 \\sim O1A: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
within 2A
Uanis(C17A) = Uanis(C17)
4. Rigid body (RIGU) restrains
 C17, C18, C17A, C18A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C15, C16, C15A, C16A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O1, O1A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C17A)=Sof(H17C)=Sof(H17D)=Sof(C18A)=Sof(H18D)=Sof(H18E)=Sof(H18F)=1-FVAR(1)
 Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(C18)=Sof(H18A)=Sof(H18B)=Sof(H18C)=FVAR(1)
 Sof(C15A)=Sof(H15C)=Sof(H15D)=Sof(C16A)=Sof(H16D)=Sof(H16E)=Sof(H16F)=1-FVAR(2)
 Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(H16C)=FVAR(2)
 Sof(O1A)=1-FVAR(3)
 Sof(O1)=FVAR(3)
6.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B), C7(H7A,H7B), C9(H9A,H9B), C11(H11A,H11B), C13(H13A,
 H13B), C19(H19A,H19B), C21(H21A,H21B), C15(H15A,H15B), C17(H17A,H17B),
 C15A(H15C,H15D), C17A(H17C,H17D)
6.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C6(H6A,H6B,H6C), C8(H8A,H8B,H8C), C10(H10A,H10B,H10C),
 C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C20(H20A,H20B,H20C), C22(H22A,H22B,
 H22C), C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C16A(H16D,H16E,H16F),
 C18A(H18D,H18E,H18F)
6.c Boron cage BH refined with riding coordinates:
 B2(H2), B3(H3), B4(H4), B5(H5), B6(H6), B7(H7), B8(H8), B9(H9)
;
_shelx_res_checksum              53521
_olex2_submission_original_sample_id 'SK-Et diester'
_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 1.456
_oxdiff_exptl_absorpt_empirical_full_min 0.728