Pd-Catalysed synthesis of carborane sulfides from carborane thiols.
Minematsu, Natsuki; Nishii, Yuji; Hirano, Koji; Chemical communications (Cambridge, England)  (2024) –; doi:10.1039/d4cc03934c

data_7133912
_publ_section_title
;
 Pd-Catalysed synthesis of carborane sulfides from carborane thiols.
;
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_paper_doi               10.1039/d4cc03934c
_journal_year                    2024
_chemical_formula_moiety         'C10 H20 B10 O2 S'
_chemical_formula_sum            'C10 H20 B10 O2 S'
_chemical_formula_weight         312.42
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2kj7t5
_audit_creation_date             2023-10-26
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-07-09 deposited with the CCDC.	2024-10-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7117(2)
_cell_length_b                   7.2609(2)
_cell_length_c                   26.2516(7)
_cell_measurement_reflns_used    6698
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      74.6930
_cell_measurement_theta_min      5.3350
_cell_volume                     1660.54(7)
_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 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_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    -78.00 -52.00   0.50    1.11    --  -42.80 151.00-155.00   52
  2  \w    -68.00 -43.00   0.50    1.11    --  -42.80 122.00  42.00   50
  3  \w   -101.00 -57.00   0.50    1.11    --  -42.80-151.00 159.00   88
  4  \w     60.00 111.00   0.50    1.11    --   42.80-151.00 159.00  102
  5  \w     58.00  85.00   0.50    1.11    --   42.80 151.00-155.00   54
  6  \w     46.00  75.00   0.50    1.11    --   42.80-122.00 -38.00   58
  7  \w     67.00  92.00   0.50    4.46    --   96.50-122.00 -38.00   50
  8  \w     91.00 117.00   0.50    4.46    --   96.50 122.00  42.00   52
  9  \w     35.00 128.00   0.50    4.46    --   96.50-151.00 159.00  186
 10  \w   -130.00 -75.00   0.50    4.46    -- -108.01 151.00-155.00  110
 11  \w   -150.00-125.00   0.50    4.46    -- -108.01-122.00 -38.00   50
 12  \w   -110.00 -38.00   0.50    4.46    -- -108.01 122.00  42.00  144
 13  \w   -110.00 -85.00   0.50    4.46    -- -108.01-151.00 159.00   50
 14  \w    -37.00   0.00   0.50    1.11    --   42.80 -19.00 -60.00   74
 15  \w    -31.00   2.00   0.50    1.11    --   42.80 -19.00 -90.00   66
 16  \w    -31.00  20.00   0.50    1.11    --   42.80 -37.00  60.00  102
 17  \w    -32.00   4.00   0.50    1.11    --   42.80 -19.00-180.00   72
 18  \w    -35.00   2.00   0.50    1.11    --   42.80 -19.00 -30.00   74
 19  \w     39.00 115.00   0.50    1.11    --   42.80  57.00-150.00  152
 20  \w     80.00 140.00   0.50    4.46    --   96.50  77.00 -60.00  120
 21  \w     46.00  98.00   0.50    4.46    --   96.50 -94.00 120.00  104
 22  \w    -65.00 -35.00   0.50    4.46    -- -108.01  45.00-180.00   60
 23  \w    -55.00 -30.00   0.50    4.46    -- -108.01  30.00  90.00   50
 24  \w    -56.00 -29.00   0.50    4.46    -- -108.01  30.00 -60.00   54
 25  \w   -157.00-131.00   0.50    4.46    -- -108.01 -30.00-180.00   52
 26  \w    -56.00 -30.00   0.50    4.46    -- -108.01  30.00 -30.00   52
 27  \w    -90.00 -36.00   0.50    4.46    -- -108.01  61.00  60.00  108
 28  \w    -67.00 -32.00   0.50    4.46    -- -108.01  45.00-150.00   70
 29  \w   -177.00 -84.00   0.50    4.46    -- -108.01 -30.00 -90.00  186
 30  \w    -57.00 -30.00   0.50    4.46    -- -108.01  30.00  30.00   54
 31  \w    -57.00 -32.00   0.50    4.46    -- -108.01  30.00-180.00   50
 32  \w   -117.00 -90.00   0.50    4.46    -- -108.01 -15.00  60.00   54
 33  \w    -96.00 -37.00   0.50    4.46    -- -108.01 125.00 -60.00  118
 34  \w   -159.00-134.00   0.50    4.46    -- -108.01 -15.00  60.00   50
 35  \w   -121.00 -34.00   0.50    4.46    -- -108.01  77.00-120.00  174
 36  \w   -109.00 -45.00   0.50    4.46    -- -108.01 115.00-168.97  128
 37  \w    -55.00 -29.00   0.50    4.46    -- -108.01  30.00 120.00   52
 38  \w    -63.00 -38.00   0.50    4.46    -- -108.01  45.00  60.00   50
 39  \w   -127.00 -93.00   0.50    4.46    -- -108.01 -30.00-180.00   68
 40  \w    -68.00 -43.00   0.50    4.46    -- -108.01  45.00 -90.00   50
 41  \w   -108.00 -83.00   0.50    4.46    -- -108.01 112.00-120.82   50
 42  \w   -109.00 -38.00   0.50    4.46    -- -108.01 125.00 -90.00  142
 43  \w   -165.00 -94.00   0.50    4.46    -- -108.01 -45.00  30.00  142
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0193809000
_diffrn_orient_matrix_UB_12      -0.0016271000
_diffrn_orient_matrix_UB_13      0.0583207000
_diffrn_orient_matrix_UB_21      0.0494890000
_diffrn_orient_matrix_UB_22      0.2036500000
_diffrn_orient_matrix_UB_23      0.0022096000
_diffrn_orient_matrix_UB_31      -0.1687083000
_diffrn_orient_matrix_UB_32      0.0594771000
_diffrn_orient_matrix_UB_33      -0.0060245000
_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  0.0940
_diffrn_reflns_av_unetI/netI     0.0564
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            18361
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.101
_diffrn_reflns_theta_min         3.367
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.663
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87982
_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    1.250
_exptl_crystal_description       plate
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.620
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.14(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.762
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         3349
_refine_ls_number_restraints     118
_refine_ls_restrained_S_all      1.734
_refine_ls_R_factor_all          0.0996
_refine_ls_R_factor_gt           0.0880
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2467
_refine_ls_wR_factor_ref         0.2553
_reflns_Friedel_coverage         0.696
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                2745
_reflns_number_total             3349
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc03934c2.cif
_cod_data_source_block           231026_mn34
_cod_database_code               7133912
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C10 H20 B10 S O2'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 S001-B009 \\sim S0-B009
 with sigma of 0.02
 S001-C00M \\sim S0-C00N
 with sigma of 0.02
 C00D-O00J \\sim C00E-O00K
 with sigma of 0.02
 C00F-O00J \\sim C3-O00K
 with sigma of 0.02
 C00F-C00L \\sim C3-C1
 with sigma of 0.02
 C00F-C00M \\sim C3-C00N
 with sigma of 0.02
 C00L-C00S \\sim C1-C00T
 with sigma of 0.02
 C00M-C5 \\sim C00N-C5A
 with sigma of 0.02
 C00P-C00S \\sim C00Q-C00T
 with sigma of 0.02
 C00P-C5 \\sim C00Q-C5A
 with sigma of 0.02
 O2-C6 \\sim O2A-C6A
 with sigma of 0.02
 O2-C5 \\sim O2A-C5A
 with sigma of 0.02
 S001-C00F \\sim S0-C3
 with sigma of 0.04
 S001-C5 \\sim S0-C5A
 with sigma of 0.04
 B009-C00M \\sim B009-C00N
 with sigma of 0.04
 C00D-C00F \\sim C00E-C3
 with sigma of 0.04
 C00F-C00S \\sim C3-C00T
 with sigma of 0.04
 C00F-C5 \\sim C3-C5A
 with sigma of 0.04
 O00J-C00L \\sim O00K-C1
 with sigma of 0.04
 O00J-C00M \\sim O00K-C00N
 with sigma of 0.04
 C00L-C00M \\sim C1-C00N
 with sigma of 0.04
 C00L-C00P \\sim C1-C00Q
 with sigma of 0.04
 C00M-C00P \\sim C00N-C00Q
 with sigma of 0.04
 C00M-O2 \\sim C00N-O2A
 with sigma of 0.04
 C00P-O2 \\sim C00Q-O2A
 with sigma of 0.04
 C00S-C5 \\sim C00T-C5A
 with sigma of 0.04
 C6-C5 \\sim C6A-C5A
 with sigma of 0.04
3. Rigid bond restraints
 C5, C00M, C00F, C00L, C00S, C00P
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C3, C00N, C5A, C00Q, C00T, C1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C1 \\sim C3 \\sim C00N \\sim C5A \\sim C00Q \\sim C00T: within 1.7A with sigma
of 0.04 and sigma for terminal atoms of 0.08 within 1.7A
C5 \\sim C00M \\sim C00F \\sim C00L \\sim C00S \\sim C00P: within 1.7A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 1.7A
: with sigma of 0.1 and sigma for terminal atoms of 0.2
5. Others
 Sof(S0)=Sof(C00N)=Sof(C5A)=Sof(O2A)=Sof(C6A)=Sof(H6AA)=Sof(H6AB)=Sof(H6AC)=
 Sof(C00Q)=Sof(H00Q)=Sof(C00T)=Sof(H00T)=Sof(C1)=Sof(H1)=Sof(C3)=Sof(O00K)=
 Sof(C00E)=Sof(H00K)=Sof(H00M)=Sof(H00N)=1-FVAR(1)
 Sof(S001)=Sof(C00D)=Sof(H00D)=Sof(H00E)=Sof(H00F)=Sof(C00F)=Sof(O00J)=
 Sof(C00L)=Sof(H00L)=Sof(C00M)=Sof(C00P)=Sof(H00P)=Sof(C00S)=Sof(H00S)=Sof(O2)=
 Sof(C6)=Sof(H6A)=Sof(H6B)=Sof(H6C)=Sof(C5)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C00L(H00L), C00P(H00P), C00S(H00S), C00Q(H00Q), C00T(H00T), C1(H1)
6.b Idealised Me refined as rotating group:
 C00D(H00D,H00E,H00F), C6(H6A,H6B,H6C), C6A(H6AA,H6AB,H6AC), C00E(H00K,H00M,
 H00N)
6.c Boron cage BH refined with riding coordinates:
 B005(H005), B006(H006), B008(H008), B00A(H00A), B00B(H00B), B00C(H00C),
 B00E(H00G), C00G(H00H), B00H(H00I), B00I(H00J), C9(H9)
;
_shelx_res_checksum              99436
_shelx_hkl_checksum              37214
_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 1.639
_oxdiff_exptl_absorpt_empirical_full_min 0.726