Variation in pnictogen-oxygen bonding unlocks greatly enhanced Brønsted basicity for the monomeric stibine oxide.
Wenger, John S.; Getahun, Addis; Johnstone, Timothy C.; Dalton transactions (Cambridge, England : 2003)  (2023) –; doi:10.1039/d3dt02113k

data_7713640
_publ_section_title
;
 Variation in pnictogen-oxygen bonding unlocks greatly enhanced
 Br&#xf8;nsted basicity for the monomeric stibine oxide.
;
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_paper_doi               10.1039/d3dt02113k
_journal_year                    2023
_chemical_formula_moiety         'C36 H52 O Sb, C F3 O3 S'
_chemical_formula_sum            'C37 H52 F3 O4 S Sb'
_chemical_formula_weight         771.59
_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             2022-07-07
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-03-21 deposited with the CCDC.	2023-07-28 downloaded from the CCDC.
;
_cell_angle_alpha                90.2560(10)
_cell_angle_beta                 98.4430(10)
_cell_angle_gamma                105.1700(10)
_cell_formula_units_Z            2
_cell_length_a                   10.19520(10)
_cell_length_b                   12.58260(10)
_cell_length_c                   14.95020(10)
_cell_measurement_reflns_used    38568
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.1970
_cell_measurement_theta_min      2.9670
_cell_volume                     1829.10(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.53a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.53a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.53a (Rigaku OD, 2022)'
_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      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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    107.00 175.00   0.50    0.38    --  105.75  77.00 150.00  136
  2  \w    102.00 147.00   0.50    0.38    --  105.75  77.00  60.00   90
  3  \w    152.00 178.00   0.50    0.38    --  105.75  77.00  60.00   52
  4  \w    106.00 178.00   0.50    0.38    --  105.75  66.00  22.00  144
  5  \w    100.00 155.00   0.50    0.38    --  105.75  38.00 -30.00  110
  6  \w     79.00 119.00   0.50    0.09    --   49.66  66.00  22.00   80
  7  \w    105.00 165.00   0.50    0.38    --  105.75  19.00 120.00  120
  8  \w     34.00  60.00   0.50    0.38    --  105.75 -57.00  30.00   52
  9  \w     38.00  65.00   0.50    0.38    --  105.75 -57.00 -30.00   54
 10  \w     35.00  60.00   0.50    0.38    --  105.75 -66.00-111.00   50
 11  \w     34.00  63.00   0.50    0.38    --  105.75 -57.00-180.00   58
 12  \w      2.00  66.00   0.50    0.09    --   49.66 -66.00-111.00  128
 13  \w     35.00  60.00   0.50    0.38    --  105.75 -57.00 -60.00   50
 14  \w     34.00  66.00   0.50    0.38    --  105.75 -57.00 120.00   64
 15  \w     35.00  62.00   0.50    0.38    --  105.75 -57.00 150.00   54
 16  \w     46.00 106.00   0.50    0.38    --  105.75 -99.00 120.00  120
 17  \w     82.00 110.00   0.50    0.38    --  105.75-125.00 120.00   56
 18  \w     35.00  76.00   0.50    0.38    --  105.75-125.00 120.00   82
 19  \w     74.00 102.00   0.50    0.38    --  105.75 -99.00   0.00   56
 20  \w     34.00 104.00   0.50    0.38    --  105.75-125.00 -30.00  140
 21  \w     51.00  76.00   0.50    0.38    --  105.75 -99.00 -60.00   50
 22  \w     81.00 106.00   0.50    0.38    --  105.75 -99.00 -60.00   50
 23  \w     67.00 106.00   0.50    0.38    --  105.75 -99.00-120.00   78
 24  \w     67.00  93.00   0.50    0.38    --  105.75 -99.00-180.00   52
 25  \w     36.00 100.00   0.50    0.38    --  105.75 -99.00-150.00  128
 26  \w     37.00  73.00   0.50    0.38    --  105.75-125.00 -90.00   72
 27  \w     41.00  66.00   0.50    0.38    --  105.75 -99.00   0.00   50
 28  \w     75.00 100.00   0.50    0.38    --  105.75 -99.00  30.00   50
 29  \w     51.00  98.00   0.50    0.38    --  105.75 -99.00  60.00   94
 30  \w    -30.00  17.00   0.50    0.09    --  -49.66  66.00  22.00   94
 31  \w    -64.00 -15.00   0.50    0.38    --  -84.25  57.00 -60.00   98
 32  \w    -66.00 -33.00   0.50    0.38    --  -84.25  66.00  22.00   66
 33  \w    -42.00 -15.00   0.50    0.38    --  -84.25  38.00  30.00   54
 34  \w    -18.00  10.00   0.50    0.09    --  -49.66  19.00  30.00   56
 35  \w    -41.00 -15.00   0.50    0.38    --  -84.25  38.00 150.00   52
 36  \w    -42.00 -17.00   0.50    0.38    --  -84.25  38.00 120.00   50
 37  \w   -151.00-100.00   0.50    0.38    --  -84.25 -77.00   0.00  102
 38  \w   -151.00 -93.00   0.50    0.38    --  -84.25 -66.00-111.00  116
 39  \w    -66.00 -34.00   0.50    0.09    --  -49.66 -66.00-111.00   64
 40  \w   -116.00 -85.00   0.50    0.09    --  -49.66 -57.00 -90.00   62
 41  \w   -119.00 -83.00   0.50    0.09    --  -49.66 -66.00-111.00   72
 42  \w   -120.00 -91.00   0.50    0.09    --  -49.66-125.00 -30.00   58
 43  \w   -156.00-111.00   0.50    0.38    --  -84.25-125.00  30.00   90
 44  \w   -117.00 -90.00   0.50    0.09    --  -49.66-125.00-150.00   54
 45  \w   -120.00 -92.00   0.50    0.09    --  -49.66-125.00-180.00   56
 46  \w   -153.00-127.00   0.50    0.38    --  -84.25 -66.00-111.00   52
 47  \w    -13.00  12.00   0.50    0.09    --   12.00  87.00 164.93   50
 48  \w      0.00  26.00   0.50    0.09    --   20.00  75.00  80.47   52
 49  \w      6.00  31.00   0.50    0.09    --   24.00  70.00 -39.69   50
 50  \w    -44.00 -19.00   0.50    0.09    --  -32.00 -63.00 -93.61   50
 51  \w    -42.00 -17.00   0.50    0.09    --  -32.00 -64.00-179.03   50
 52  \w     17.00  42.00   0.50    0.09    --   32.00  63.00-145.65   50
 53  \w    -48.00 -23.00   0.50    0.09    --  -36.00 -61.00 107.58   50
 54  \w     22.00  47.00   0.50    0.09    --   36.00  60.00 103.43   50
 55  \w    -56.00 -31.00   0.50    0.09    --  -40.00 -58.00  34.95   50
 56  \w     27.00  52.00   0.50    0.09    --   40.00  58.00-160.80   50
 57  \w    -76.00 -36.00   0.50    0.09    --  -48.00 -55.00 -30.67   80
 58  \w     33.00  61.00   0.50    0.09    --   49.41  66.00  22.00   56
 59  \w    -66.00 -40.00   0.50    0.09    --  -52.00 -56.00 167.34   52
 60  \w    -81.00 -40.00   0.50    0.09    --  -52.00 -56.00 -88.89   82
 61  \w    -72.00 -46.00   0.50    0.09    --  -56.00 -54.00 144.37   52
 62  \w    -75.00 -50.00   0.50    0.09    --  -60.00 -51.00 -72.44   50
 63  \w    -88.00 -48.00   0.50    0.09    --  -60.00 -56.00  75.06   80
 64  \w    -88.00 -48.00   0.50    0.09    --  -60.00 -53.00  18.72   80
 65  \w   -131.00-105.00   0.50    0.09    --  -60.00 -56.00  75.06   52
 66  \w    -74.00 -48.00   0.50    0.09    --  -60.00 -54.00  90.00   52
 67  \w    -82.00 -48.00   0.50    0.09    --  -60.00 -54.00 118.39   68
 68  \w    -73.00 -48.00   0.50    0.09    --  -60.00 -54.00-161.26   50
 69  \w    -74.00 -48.00   0.50    0.09    --  -60.00 -53.00-128.29   52
 70  \w   -125.00 -98.00   0.50    0.09    --  -60.00 -53.00  18.72   54
 71  \w    -81.00 -56.00   0.50    0.38    --  -68.00 -54.00  15.37   50
 72  \w   -131.00-105.00   0.50    0.38    --  -68.00 -54.00  15.37   52
 73  \w    107.00 134.00   0.50    0.09    --   68.00  55.00 102.93   54
 74  \w     56.00  81.00   0.50    0.09    --   68.00  55.00 102.93   50
 75  \w    -86.00 -60.00   0.50    0.38    --  -72.00 -54.00 -78.99   52
 76  \w    -92.00 -66.00   0.50    0.38    --  -76.00 -55.00 154.32   52
 77  \w    -89.00 -63.00   0.50    0.38    --  -76.00 -56.00 139.03   52
 78  \w    -90.00 -64.00   0.50    0.38    --  -76.00 -54.00   2.54   52
 79  \w    -91.00 -65.00   0.50    0.38    --  -76.00 -56.00 -54.22   52
 80  \w    -89.00 -64.00   0.50    0.38    --  -76.00 -56.00 -26.17   50
 81  \w    -89.00 -63.00   0.50    0.38    --  -76.00 -56.00-164.97   52
 82  \w    -89.00 -64.00   0.50    0.38    --  -76.00 -56.00 -82.81   50
 83  \w    -93.00 -68.00   0.50    0.38    --  -80.00 -53.00 -42.68   50
 84  \w   -150.00-125.00   0.50    0.38    --  -80.00 -53.00 -42.68   50
 85  \w    -99.00 -72.00   0.50    0.38    --  -84.25 -54.00-173.17   54
 86  \w   -104.00 -72.00   0.50    0.38    --  -84.25 -55.00  26.77   64
 87  \w    -98.00 -72.00   0.50    0.38    --  -84.25 -54.00 110.78   52
 88  \w   -101.00 -75.00   0.50    0.38    --  -84.25 -51.00 -10.78   52
 89  \w    -97.00 -72.00   0.50    0.38    --  -84.25 -55.00  72.87   50
 90  \w    -98.00 -72.00   0.50    0.38    --  -84.25 -54.00-140.78   52
 91  \w   -104.00 -75.00   0.50    0.38    --  -84.25 -54.00 105.05   58
 92  \w   -100.00 -74.00   0.50    0.38    --  -84.25 -54.00   1.11   52
 93  \w   -133.00 -74.00   0.50    0.38    --  -84.25 -51.00 135.40  118
 94  \w    -98.00 -73.00   0.50    0.38    --  -84.25 -54.00 126.21   50
 95  \w   -105.00 -72.00   0.50    0.38    --  -84.25 -54.00 -73.29   66
 96  \w   -100.00 -74.00   0.50    0.38    --  -84.25 -55.00 177.47   52
 97  \w   -140.00-114.00   0.50    0.38    --  -84.25 -55.00 177.47   52
 98  \w    -99.00 -73.00   0.50    0.38    --  -84.25 -54.00-148.87   52
 99  \w    -42.00 -17.00   0.50    0.38    --  -84.25  38.00 -90.00   50
100  \w   -103.00 -73.00   0.50    0.38    --  -84.25 -55.00-106.28   60
101  \w    -93.00 -68.00   0.50    0.38    --  -84.25 -66.00-111.00   50
102  \w    -97.00 -72.00   0.50    0.38    --  -84.25 -55.00  44.99   50
103  \w   -102.00 -77.00   0.50    0.38    --  -84.25 -56.00 -92.31   50
104  \w    -99.00 -73.00   0.50    0.38    --  -84.25 -53.00  51.28   52
105  \w   -100.00 -74.00   0.50    0.38    --  -84.25 -51.00  87.18   52
106  \w    104.00 131.00   0.50    0.38    --  105.75  57.00 -30.00   54
107  \w     71.00  97.00   0.50    0.38    --  105.75-125.00   0.00   52
108  \w     36.00  61.00   0.50    0.38    --  105.75-125.00   0.00   50
109  \w    141.00 168.00   0.50    0.38    --  105.75  57.00-150.00   54
110  \w    103.00 129.00   0.50    0.38    --  105.75  57.00-150.00   52
111  \w    137.00 175.00   0.50    0.38    --  105.75  57.00-120.00   76
112  \w    141.00 177.00   0.50    0.38    --  105.75  57.00-180.00   72
113  \w     95.00 130.00   0.50    0.38    --  105.75  57.00-120.00   70
114  \w     93.00 125.00   0.50    0.38    --  105.75  57.00-180.00   64
115  \w    141.00 167.00   0.50    0.38    --  105.75  57.00 -90.00   52
116  \w     94.00 125.00   0.50    0.38    --  105.75  57.00 -90.00   62
117  \w     99.00 151.00   0.50    0.38    --  105.75  38.00 150.00  104
118  \w     94.00 119.00   0.50    0.38    --  105.75  57.00 -60.00   50
119  \w    101.00 150.00   0.50    0.38    --  105.75  38.00  60.00   98
120  \w     96.00 128.00   0.50    0.38    --  105.75  57.00   0.00   64
121  \w    140.00 168.00   0.50    0.38    --  105.75  57.00 -30.00   56
;
_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      -0.1442352000
_diffrn_orient_matrix_UB_12      -0.0405214000
_diffrn_orient_matrix_UB_13      -0.0564170000
_diffrn_orient_matrix_UB_21      -0.0286853000
_diffrn_orient_matrix_UB_22      -0.1045907000
_diffrn_orient_matrix_UB_23      0.0550348000
_diffrn_orient_matrix_UB_31      -0.0589488000
_diffrn_orient_matrix_UB_32      0.0595295000
_diffrn_orient_matrix_UB_33      0.0682841000
_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  0.0480
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            52573
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.073
_diffrn_reflns_theta_max         67.073
_diffrn_reflns_theta_min         2.991
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.948
_exptl_absorpt_correction_T_max  0.82604
_exptl_absorpt_correction_T_min  0.82087
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.53a (Rigaku Oxford Diffraction, 2022)
Spherical absorption correction
using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_description       sphere
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_crystal_size_rad          0.037
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     431
_refine_ls_number_reflns         6525
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0209
_refine_ls_R_factor_gt           0.0198
_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^)+(0.0230P)^2^+0.9736P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0489
_refine_ls_wR_factor_ref         0.0494
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6264
_reflns_number_total             6525
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt02113k2.cif
_cod_data_source_block           2a
_cod_database_code               7713640
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C37 H52 O4 Sb1 F3 S1'
_chemical_oxdiff_usercomment     'Dipp3SbOH CF3SO3 JSW0564'
_shelx_estimated_absorpt_t_max   0.681
_shelx_estimated_absorpt_t_min   0.574
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O1-H1
 0.84 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C17(H17), C37(H37), C38(H38), C18(H18), C28(H28), C27(H27)
3.b Aromatic/amide H refined with riding coordinates:
 C33(H33), C34(H34), C13(H13), C35(H35), C25(H25), C14(H14), C15(H15),
 C24(H24), C23(H23)
3.c Idealised Me refined as rotating group:
 C371(H37A,H37B,H37C), C171(H17A,H17B,H17C), C172(H17D,H17E,H17F), C182(H18A,
 H18B,H18C), C271(H27A,H27B,H27C), C282(H28A,H28B,H28C), C372(H37D,H37E,H37F),
 C381(H38A,H38B,H38C), C382(H38D,H38E,H38F), C281(H28D,H28E,H28F), C181(H18D,
 H18E,H18F), C272(H27D,H27E,H27F)
;
_shelx_res_checksum              84543
_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 1.302
_oxdiff_exptl_absorpt_empirical_full_min 0.737