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_7713642
_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, C6 H2 N3 O7'
_chemical_formula_sum            'C42 H54 N3 O8 Sb'
_chemical_formula_weight         850.63
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yac'
_space_group_name_H-M_alt        'P 1 n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-07-16
_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
_cell_angle_beta                 93.444(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4423(2)
_cell_length_b                   20.8325(5)
_cell_length_c                   18.7820(4)
_cell_measurement_reflns_used    34004
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      39.8390
_cell_measurement_theta_min      2.3760
_cell_volume                     4078.44(15)
_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      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -60.00  19.00   0.50    6.79    --  -33.17  90.00  56.00  158
  2  \w    -34.00  62.00   0.50    6.79    --   33.17 -90.00 -57.00  192
  3  \w    -60.00 -23.00   0.50    6.79    --  -33.17 -57.00  90.00   74
  4  \w    -47.00 -21.00   0.50    6.79    --  -33.17 -57.00 150.00   52
  5  \w     29.00  57.00   0.50    6.79    --   33.17  57.00  30.00   56
  6  \w    -39.00   6.00   0.50    6.79    --   33.17 -19.00 -30.00   90
  7  \w    -38.00   0.00   0.50    6.79    --   33.17 -19.00   0.00   76
  8  \w     18.00  43.00   0.50    6.79    --   33.17  57.00 -60.00   50
  9  \w     18.00  43.00   0.50    6.79    --   33.17  57.00  60.00   50
 10  \w    -38.00  23.00   0.50    6.79    --   33.17 -38.00-150.00  122
;
_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      -0.0057620000
_diffrn_orient_matrix_UB_12      0.0309594000
_diffrn_orient_matrix_UB_13      -0.0155852000
_diffrn_orient_matrix_UB_21      0.0663339000
_diffrn_orient_matrix_UB_22      -0.0003442000
_diffrn_orient_matrix_UB_23      -0.0062114000
_diffrn_orient_matrix_UB_31      -0.0140592000
_diffrn_orient_matrix_UB_32      -0.0141682000
_diffrn_orient_matrix_UB_33      -0.0339051000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            32156
_diffrn_reflns_point_group_measured_fraction_full 0.870
_diffrn_reflns_point_group_measured_fraction_max 0.870
_diffrn_reflns_theta_full        25.123
_diffrn_reflns_theta_max         25.123
_diffrn_reflns_theta_min         2.185
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.731
_exptl_absorpt_correction_T_max  0.86900
_exptl_absorpt_correction_T_min  0.86900
_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    1.385
_exptl_crystal_description       sphere
_exptl_crystal_F_000             1768
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_exptl_crystal_size_rad          0.094
_refine_diff_density_max         0.904
_refine_diff_density_min         -0.752
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 4474 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.008(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1087
_refine_ls_number_reflns         12674
_refine_ls_number_restraints     472
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0310
_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^)+(0.0292P)^2^+0.6778P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0693
_refine_ls_wR_factor_ref         0.0709
_reflns_Friedel_coverage         0.739
_reflns_Friedel_fraction_full    0.740
_reflns_Friedel_fraction_max     0.740
_reflns_number_gt                11794
_reflns_number_total             12674
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt02113k2.cif
_cod_data_source_block           4a
_cod_database_code               7713642
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C42 H54 Sb1 O8 N3'
_chemical_oxdiff_usercomment     'Dipp3SbO Picric Acid - JSW0404'
_shelx_estimated_absorpt_t_max   0.905
_shelx_estimated_absorpt_t_min   0.827
_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
 O11-H11
 0.84 with sigma of 0.02
 O21-H21
 0.84 with sigma of 0.02
 C46-N11A \\sim C46-N11B
 with sigma of 0.01
 N11A-O13A \\sim N11A-O14A \\sim N11B-O13B \\sim N11B-O14B
 with sigma of 0.01
 O13A-O14A \\sim O13B-O14B
 with sigma of 0.01
 C46-O13A \\sim C46-O14A \\sim C46-O13B \\sim C46-O14B
 with sigma of 0.01
 C86-N21A \\sim C86-N21B
 with sigma of 0.01
 N21A-O23A \\sim N21A-O24A \\sim N21B-O23B \\sim N21B-O24B
 with sigma of 0.01
 O23A-O24A \\sim O23B-O24B
 with sigma of 0.01
 C86-O23A \\sim C86-O24A \\sim C86-O23B \\sim C86-O24B
 with sigma of 0.01
 C42-N13A \\sim C42-N13B
 with sigma of 0.01
 N13A-O17A \\sim N13A-O18A \\sim N13B-O17B \\sim N13B-O18B
 with sigma of 0.01
 O17A-O18A \\sim O17B-O18B
 with sigma of 0.01
 C42-O17A \\sim C42-O18A \\sim C42-O17B \\sim C42-O18B
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C12 \\sim C17 \\sim C171 \\sim C172 \\sim C13 \\sim C14 \\sim C15 \\sim C16
\\sim C11 \\sim C18 \\sim C182 \\sim C181: within 2A with sigma of 0.02 and
sigma for terminal atoms of 0.04 within 2A
N11A \\sim N11B \\sim O14A \\sim O14B \\sim O13A \\sim O13B: within 2A with
sigma of 0.005 and sigma for terminal atoms of 0.01 within 2A
N21A \\sim N21B \\sim O24A \\sim O24B \\sim O23A \\sim O23B: within 2A with
sigma of 0.005 and sigma for terminal atoms of 0.01 within 2A
N13A \\sim N13B \\sim O18A \\sim O18B \\sim O17A \\sim O17B: within 2A with
sigma of 0.005 and sigma for terminal atoms of 0.01 within 2A
4. Rigid body (RIGU) restrains
 C12, C17, C171, C172, C13, C14, C15, C16, C11, C18, C182, C181
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 N11A, N11B, O14A, O14B, O13A, O13B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 N21A, N21B, O24A, O24B, O23A, O23B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 N13A, N13B, O18A, O18B, O17A, O17B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(N11B)=Sof(O13B)=Sof(O14B)=Sof(N21B)=Sof(O23B)=Sof(O24B)=Sof(N13B)=
 Sof(O17B)=Sof(O18B)=1-FVAR(1)
 Sof(N11A)=Sof(O13A)=Sof(O14A)=Sof(N21A)=Sof(O23A)=Sof(O24A)=Sof(N13A)=
 Sof(O17A)=Sof(O18A)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C17(H17), C18(H18), C68(H68), C77(H77), C67(H67), C58(H58), C38(H38),
 C57(H57), C28(H28), C78(H78), C37(H37), C27(H27)
6.b Aromatic/amide H refined with riding coordinates:
 C25(H25), C55(H55), C65(H65), C64(H64), C83(H83), C13(H13), C75(H75),
 C14(H14), C85(H85), C35(H35), C24(H24), C63(H63), C73(H73), C74(H74), C15(H15),
  C54(H54), C34(H34), C43(H43), C33(H33), C45(H45), C23(H23), C53(H53)
6.c Idealised Me refined as rotating group:
 C271(H27A,H27B,H27C), C371(H37A,H37B,H37C), C772(H77A,H77B,H77C), C581(H58A,
 H58B,H58C), C671(H67A,H67B,H67C), C571(H57A,H57B,H57C), C281(H28A,H28B,H28C),
 C182(H18A,H18B,H18C), C172(H17A,H17B,H17C), C682(H68A,H68B,H68C), C782(H78A,
 H78B,H78C), C381(H38A,H38B,H38C), C171(H17D,H17E,H17F), C572(H57D,H57E,H57F),
 C781(H78D,H78E,H78F), C272(H27D,H27E,H27F), C382(H38D,H38E,H38F), C372(H37D,
 H37E,H37F), C681(H68D,H68E,H68F), C181(H18D,H18E,H18F), C771(H77D,H77E,H77F),
 C282(H28D,H28E,H28F), C672(H67D,H67E,H67F), C582(H58D,H58E,H58F)
;
_shelx_res_checksum              77977
_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 1.314
_oxdiff_exptl_absorpt_empirical_full_min 0.752