Harnessing transient CAAC-stabilized mesitylborylenes for chalcogen activation.
Michel, Maximilian; Endres, Lukas; Fantuzzi, Felipe; Krummenacher, Ivo; Braunschweig, Holger; Chemical science 16 (2025) 5632–5639; doi:10.1039/d5sc00154d

data_1574011
_publ_section_title
;
 Harnessing transient CAAC-stabilized mesitylborylenes for chalcogen
 activation.
;
_journal_issue                   13
_journal_name_full               'Chemical science'
_journal_page_first              5632
_journal_page_last               5639
_journal_paper_doi               10.1039/d5sc00154d
_journal_volume                  16
_journal_year                    2025
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C29 H42 B N Se, C4 H8 O'
_chemical_formula_sum            'C33 H50 B N O Se'
_chemical_formula_weight         566.51
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2024-05-23
_audit_creation_method           'CIF-fill 1.5c (K.Radacki, 2005-23)'
_audit_update_record
;
2024-10-18 deposited with the CCDC.	2025-02-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.23860(10)
_cell_length_b                   14.04470(10)
_cell_length_c                   15.38680(10)
_cell_measurement_reflns_used    45877
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.7090
_cell_measurement_theta_min      4.2130
_cell_volume                     3077.00(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)''
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 HPA
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HyPix Arc150'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w    -97.00 -22.00   0.50    0.08    --  -69.46 126.00 -90.00  150
  2  \w    -96.00 -31.00   0.50    0.08    --  -76.38 114.00 -16.00  130
  3  \w    -80.00 -14.00   0.50    0.08    --  -60.08 114.00 -16.00  132
  4  \w    -89.00 -24.00   0.50    0.08    --  -69.46 114.00 -16.00  130
  5  \w    -92.00 -31.00   0.50    0.08    --  -76.38 112.00  30.00  122
  6  \w    -92.00 -31.00   0.50    0.08    --  -76.38 112.00  60.00  122
  7  \w    -97.00 -22.00   0.50    0.08    --  -69.46 126.00  90.00  150
  8  \w    -92.00 -31.00   0.50    0.08    --  -76.38 112.00 150.00  122
  9  \w    -92.00 -31.00   0.50    0.08    --  -76.38 112.00 -90.00  122
 10  \w    -92.00 -31.00   0.50    0.08    --  -76.38 112.00-120.00  122
 11  \w   -125.00 -91.00   0.50    0.08    --  -79.50 -61.00 -15.76   68
 12  \w   -126.00 -92.00   0.50    0.08    --  -79.50 -57.00-114.97   68
 13  \w   -125.00 -91.00   0.50    0.08    --  -79.50 -60.00  21.33   68
 14  \w   -121.00 -86.00   0.50    0.08    --  -74.00 -57.00  18.70   70
 15  \w   -121.00 -86.00   0.50    0.08    --  -74.00 -57.00  48.58   70
 16  \w   -120.00 -86.00   0.50    0.08    --  -74.00 -59.00 120.60   68
 17  \w   -117.00 -83.00   0.50    0.08    --  -70.00 -56.00 147.79   68
 18  \w   -125.00 -90.00   0.50    0.08    --  -78.00 -57.00 161.42   70
 19  \w   -127.00 -92.00   0.50    0.08    --  -79.50 -55.00  -2.53   70
 20  \w   -110.00 -75.00   0.50    0.08    --  -62.00 -51.00  70.53   70
 21  \w   -110.00 -75.00   0.50    0.08    --  -62.00 -51.00 -60.42   70
 22  \w   -118.00 -83.00   0.50    0.08    --  -70.00 -53.00-113.43   70
 23  \w   -122.00 -87.00   0.50    0.08    --  -74.00 -53.00 -88.70   70
 24  \w   -128.00 -93.00   0.50    0.08    --  -79.50 -50.00 -77.44   70
 25  \w    -91.00 -56.00   0.50    0.08    --  -42.00 -49.00  10.25   70
 26  \w   -115.00 -80.00   0.50    0.08    --  -66.00 -48.00 167.78   70
 27  \w   -129.00 -93.00   0.50    0.08    --  -79.50 -48.00  94.62   72
 28  \w   -120.00 -82.00   0.50    0.08    --  -70.00 -43.00 112.99   76
 29  \w   -128.00 -93.00   0.50    0.08    --  -79.50 -49.00  31.63   70
 30  \w   -124.00 -86.00   0.50    0.08    --  -74.00 -43.00  54.80   76
 31  \w    -99.00 -64.00   0.50    0.08    --  -50.00 -47.00 -41.14   70
 32  \w   -123.00 -87.00   0.50    0.08    --  -74.00 -46.00-144.44   72
 33  \w   -124.00 -86.00   0.50    0.08    --  -74.00 -42.00-164.05   76
 34  \w   -124.00 -86.00   0.50    0.08    --  -74.00 -42.00 -75.10   76
 35  \w   -130.00 -91.00   0.50    0.08    --  -79.50 -39.00 -53.49   78
 36  \w   -126.00 -93.00   0.50    0.08    --  -79.50-120.00  48.94   66
 37  \w   -126.00 -92.00   0.50    0.08    --  -79.50-123.00  87.43   68
 38  \w   -126.00 -93.00   0.50    0.08    --  -79.50-121.00 -32.20   66
 39  \w   -126.00 -93.00   0.50    0.08    --  -79.50-121.00-153.02   66
 40  \w     25.00  54.00   0.50    0.08    --   14.00  61.00  78.05   58
 41  \w     34.00  60.00   0.50    0.08    --   22.00  58.00 114.60   52
 42  \w     34.00  60.00   0.50    0.08    --   22.00  59.00  19.20   52
 43  \w     34.00  60.00   0.50    0.08    --   22.00  58.00 156.41   52
 44  \w     34.00  60.00   0.50    0.08    --   22.00  59.00 -20.81   52
 45  \w     30.00  56.00   0.50    0.08    --   18.00  60.00 -63.93   52
 46  \w     34.00  60.00   0.50    0.08    --   22.00  57.00-102.32   52
 47  \w     30.00  56.00   0.50    0.08    --   18.00  60.00-160.33   52
 48  \w     52.00  87.00   0.50    0.08    --   38.00  50.00-143.21   70
 49  \w     60.00  95.00   0.50    0.08    --   46.00  50.00 -76.30   70
 50  \w     29.00  79.00   0.50    0.08    --   71.20 -95.00  90.00  100
 51  \w     32.00  98.00   0.50    0.08    --   78.00-115.00 -75.54  132
 52  \w     39.00  97.00   0.50    0.08    --   84.40-114.00-107.00  116
 53  \w     31.00  93.00   0.50    0.08    --   76.43-112.00-150.00  124
 54  \w     26.00  91.00   0.50    0.08    --   71.20-114.00-107.00  130
 55  \w     31.00  96.00   0.50    0.08    --   76.43-114.00-107.00  130
 56  \w     13.00  78.00   0.50    0.08    --   58.34-114.00-107.00  130
 57  \w     39.00  93.00   0.50    0.08    --   84.40-112.00 -60.00  108
 58  \w     42.00  92.00   0.50    0.08    --   84.40 -95.00   0.00  100
 59  \w     31.00  75.00   0.50    0.08    --   76.43-112.00  30.00   88
 60  \w     42.00  92.00   0.50    0.08    --   84.40 -95.00  60.00  100
 61  \w     42.00  92.00   0.50    0.08    --   84.40 -95.00  30.00  100
 62  \w     42.00  92.00   0.50    0.08    --   84.40 -95.00  90.00  100
 63  \w     34.00  84.00   0.50    0.08    --   76.43 -95.00 120.00  100
 64  \w     42.00  92.00   0.50    0.08    --   84.40 -95.00 150.00  100
 65  \w     42.00  92.00   0.50    0.08    --   84.40 -95.00 120.00  100
 66  \w     42.00  92.00   0.50    0.08    --   84.40 -95.00 -30.00  100
 67  \w     34.00  84.00   0.50    0.08    --   76.43 -95.00 -60.00  100
 68  \w     42.00  92.00   0.50    0.08    --   84.40 -95.00 -60.00  100
 69  \w     42.00  92.00   0.50    0.08    --   84.40 -95.00-150.00  100
 70  \w     48.00 135.00   0.50    0.08    --   84.40  15.00 -90.00  174
 71  \w     48.00 135.00   0.50    0.08    --   84.40  15.00-150.00  174
 72  \w     48.00 135.00   0.50    0.08    --   84.40  15.00 120.00  174
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-R'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      0.0906478000
_diffrn_orient_matrix_UB_12      0.0320380000
_diffrn_orient_matrix_UB_13      -0.0462576000
_diffrn_orient_matrix_UB_21      0.0393336000
_diffrn_orient_matrix_UB_22      0.0367279000
_diffrn_orient_matrix_UB_23      0.0869790000
_diffrn_orient_matrix_UB_31      0.0441166000
_diffrn_orient_matrix_UB_32      -0.0983420000
_diffrn_orient_matrix_UB_33      0.0174224000
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_xray_symbol    K-L~2,3~
_diffrn_reflns_av_R_equivalents  0.0715
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            76743
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.851
_diffrn_reflns_theta_min         4.262
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    1.822
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39780
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021) Empirical 
 absorption correction using spherical harmonics, implemented in SCALE3 
 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_description       needle
_exptl_crystal_F_000             1208
_exptl_crystal_preparation
;
 For data collection the crystal was immersed in a film of perfluoropolyether 
 oil, mounted on a polyimide loop and transferred to stream of cold nitrogen 
 (Oxford Cryostream 800).
;
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.582
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 2656 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, 
 Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.002(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         6208
_refine_ls_number_restraints     211
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0350
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0589P)^2^+1.0579P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0950
_refine_ls_wR_factor_ref         0.0964
_reflns_Friedel_coverage         0.907
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                5880
_reflns_number_total             6208
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc00154d2.cif
_cod_data_source_block           1-Se
_cod_depositor_comments
'Adding full bibliography for 1574010--1574019.cif.'
_cod_database_code               1574011
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.408
_shelx_estimated_absorpt_t_max   0.931
_shelx_res_checksum              31231