Synthetic access to organyl-substituted 1,2,3-benzodiazaborines with turn-on fluorescence activity
Wüst, Leonie; Chorbacher, Johannes; Wellnitz, Tim; Nees, Samuel; Helten, Holger; Braunschweig, Holger; Chemical Science 16 (2025) 7284–7293; doi:10.1039/D5SC01500F

data_1574251
_publ_section_title
;
 Synthetic access to organyl-substituted 1,2,3-benzodiazaborines with
 turn-on fluorescence activity
;
_journal_issue                   17
_journal_name_full               'Chemical Science'
_journal_page_first              7284
_journal_page_last               7293
_journal_paper_doi               10.1039/D5SC01500F
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C16 H19 B N2 O Si'
_chemical_formula_sum            'C16 H19 B N2 O Si'
_chemical_formula_weight         294.23
_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   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2023-05-08
_audit_creation_method           'CIF-fill 1.4c (K.Radacki, 2005-23)'
_audit_update_record
;
2024-10-28 deposited with the CCDC.	2025-03-18 downloaded from the CCDC.
;
_cell_angle_alpha                84.139(2)
_cell_angle_beta                 68.542(2)
_cell_angle_gamma                74.660(2)
_cell_formula_units_Z            2
_cell_length_a                   8.8219(2)
_cell_length_b                   9.3512(2)
_cell_length_c                   10.4070(2)
_cell_measurement_reflns_used    19191
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.9790
_cell_measurement_theta_min      4.8900
_cell_volume                     770.54(3)
_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 0.992
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
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  1  \w    -82.00 -14.00   0.50    0.05    --  -60.16 118.00 133.00  136
  2  \w    -92.00 -24.00   0.50    0.05    --  -69.71 118.00 133.00  136
  3  \w    -97.00 -30.00   0.50    0.05    --  -76.30 118.00 133.00  134
  4  \w    -92.00 -31.00   0.50    0.05    --  -76.30 112.00 120.00  122
  5  \w    -92.00 -31.00   0.50    0.05    --  -76.30 112.00  90.00  122
  6  \w    -92.00 -31.00   0.50    0.05    --  -76.30 112.00  60.00  122
  7  \w   -105.00 -33.00   0.50    0.05    --  -79.50 135.00   6.21  144
  8  \w    -92.00 -31.00   0.50    0.05    --  -76.30 112.00-180.00  122
  9  \w    -92.00 -31.00   0.50    0.05    --  -76.30 112.00-120.00  122
 10  \w    -92.00 -31.00   0.50    0.05    --  -76.30 112.00 -90.00  122
 11  \w    -92.00 -31.00   0.50    0.05    --  -76.30 112.00 -60.00  122
 12  \w    -92.00 -31.00   0.50    0.05    --  -76.30 112.00   0.00  122
 13  \w   -125.00 -91.00   0.50    0.05    --  -79.50 -61.00  66.91   68
 14  \w   -124.00 -89.00   0.50    0.05    --  -78.00 -61.00  93.52   70
 15  \w   -120.00 -86.00   0.50    0.05    --  -74.00 -60.00 175.03   68
 16  \w   -125.00 -91.00   0.50    0.05    --  -79.50 -60.00 128.53   68
 17  \w   -120.00 -86.00   0.50    0.05    --  -74.00 -59.00  53.17   68
 18  \w   -121.00 -86.00   0.50    0.05    --  -74.00 -58.00  26.03   70
 19  \w   -126.00 -91.00   0.50    0.05    --  -79.50 -58.00  21.53   70
 20  \w   -117.00 -84.00   0.50    0.05    --  -70.00 -57.00 135.72   66
 21  \w   -126.00 -91.00   0.50    0.05    --  -79.50 -59.00  10.69   70
 22  \w   -121.00 -86.00   0.50    0.05    --  -74.00 -56.00 -35.55   70
 23  \w   -126.00 -92.00   0.50    0.05    --  -79.50 -57.00 -42.60   68
 24  \w   -121.00 -86.00   0.50    0.05    --  -74.00 -56.00 -82.71   70
 25  \w   -126.00 -91.00   0.50    0.05    --  -79.50 -59.00 -92.97   70
 26  \w   -122.00 -87.00   0.50    0.05    --  -74.00 -52.00 -72.41   70
 27  \w   -127.00 -92.00   0.50    0.05    --  -79.50 -54.00-115.57   70
 28  \w   -127.00 -92.00   0.50    0.05    --  -79.50 -55.00-136.00   70
 29  \w   -127.00 -92.00   0.50    0.05    --  -79.50 -53.00-159.32   70
 30  \w   -128.00 -93.00   0.50    0.05    --  -79.50 -51.00-179.22   70
 31  \w   -121.00 -86.00   0.50    0.05    --  -74.00 -57.00-165.67   70
 32  \w   -106.00 -71.00   0.50    0.05    --  -58.00 -51.00-155.84   70
 33  \w   -128.00 -93.00   0.50    0.05    --  -79.50 -51.00 -64.63   70
 34  \w   -110.00 -75.00   0.50    0.05    --  -62.00 -51.00 -33.44   70
 35  \w   -128.00 -93.00   0.50    0.05    --  -79.50 -50.00  32.86   70
 36  \w   -103.00 -67.00   0.50    0.05    --  -54.00 -46.00  34.50   72
 37  \w   -129.00 -92.00   0.50    0.05    --  -79.50 -44.00  85.25   74
 38  \w   -130.00 -92.00   0.50    0.05    --  -79.50 -42.00  92.02   76
 39  \w   -128.00 -93.00   0.50    0.05    --  -79.50 -49.00 149.38   70
 40  \w   -128.00 -93.00   0.50    0.05    --  -79.50 -49.00 130.51   70
 41  \w   -130.00 -90.00   0.50    0.05    --  -79.50 -38.00 105.05   80
 42  \w   -125.00 -85.00   0.50    0.05    --  -74.00 -34.00  94.62   80
 43  \w   -130.00 -91.00   0.50    0.05    --  -79.50 -41.00  10.54   78
 44  \w   -130.00 -91.00   0.50    0.05    --  -79.50 -40.00 -38.24   78
 45  \w   -131.00 -90.00   0.50    0.05    --  -79.50 -35.00-131.30   82
 46  \w   -125.00 -94.00   0.50    0.05    --  -79.50-119.00  71.89   62
 47  \w   -127.00 -89.00   0.50    0.05    --  -79.50-129.00 126.29   76
 48  \w    -54.00 -27.00   0.50    0.05    --  -14.00 -53.00 178.79   54
 49  \w    -54.00 -27.00   0.50    0.05    --  -14.00 -53.00 112.13   54
 50  \w    -82.00 -47.00   0.50    0.05    --  -34.00 -52.00 100.93   70
 51  \w    -54.00 -27.00   0.50    0.05    --  -14.00 -53.00 -13.23   54
 52  \w    -54.00 -26.00   0.50    0.05    --  -14.00 -55.00 -48.62   56
 53  \w    -86.00 -51.00   0.50    0.05    --  -38.00 -52.00 -94.53   70
 54  \w   -126.00 -91.00   0.50    0.05    --  -79.50-125.00-138.86   70
 55  \w    -78.00 -43.00   0.50    0.05    --  -30.00 -52.00-120.22   70
 56  \w    -75.00 -40.00   0.50    0.05    --  -26.00 -49.00 -90.03   70
 57  \w    -91.00 -56.00   0.50    0.05    --  -42.00 -48.00 -29.88   70
 58  \w    -71.00 -36.00   0.50    0.05    --  -22.00 -49.00  41.57   70
 59  \w    -99.00 -64.00   0.50    0.05    --  -50.00 -48.00  73.57   70
 60  \w    -99.00 -64.00   0.50    0.05    --  -50.00 -47.00 138.20   70
 61  \w    -74.00 -39.00   0.50    0.05    --  -26.00 -51.00 149.04   70
 62  \w     15.00  81.00   0.50    0.05    --   58.60-118.00  47.00  132
 63  \w     25.00  93.00   0.50    0.05    --   71.26-118.00  47.00  136
 64  \w     37.00  97.00   0.50    0.05    --   82.35-118.00  47.00  120
 65  \w     37.00  93.00   0.50    0.05    --   82.35-112.00 120.00  112
 66  \w     42.00  93.00   0.50    0.05    --   85.25 -97.00  40.11  102
 67  \w     40.00  90.00   0.50    0.05    --   82.35 -95.00  60.00  100
 68  \w     40.00  90.00   0.50    0.05    --   82.35 -95.00 -60.00  100
 69  \w     40.00  90.00   0.50    0.05    --   82.35 -95.00-120.00  100
 70  \w     40.00  90.00   0.50    0.05    --   82.35 -95.00-150.00  100
 71  \w     40.00  90.00   0.50    0.05    --   82.35 -95.00-180.00  100
 72  \w     40.00  90.00   0.50    0.05    --   82.35 -95.00 -30.00  100
 73  \w     40.00  90.00   0.50    0.05    --   82.35 -95.00 -90.00  100
 74  \w     40.00  90.00   0.50    0.05    --   82.35 -95.00   0.00  100
 75  \w     40.00  90.00   0.50    0.05    --   82.35 -95.00 120.00  100
 76  \w     40.00  90.00   0.50    0.05    --   82.35 -95.00 150.00  100
 77  \w     46.00 133.00   0.50    0.05    --   82.35  15.00 150.00  174
 78  \w     46.00 133.00   0.50    0.05    --   82.35  15.00  30.00  174
 79  \w     46.00 133.00   0.50    0.05    --   82.35  15.00 -30.00  174
 80  \w     46.00 133.00   0.50    0.05    --   82.35  15.00 -60.00  174
 81  \w     46.00 133.00   0.50    0.05    --   82.35  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      0.1713016000
_diffrn_orient_matrix_UB_12      -0.0968467000
_diffrn_orient_matrix_UB_13      -0.0006830000
_diffrn_orient_matrix_UB_21      -0.0754754000
_diffrn_orient_matrix_UB_22      -0.0216398000
_diffrn_orient_matrix_UB_23      0.1574060000
_diffrn_orient_matrix_UB_31      -0.0492105000
_diffrn_orient_matrix_UB_32      -0.1390556000
_diffrn_orient_matrix_UB_33      -0.0228569000
_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  0.0178
_diffrn_reflns_av_unetI/netI     0.0085
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            23656
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.105
_diffrn_reflns_theta_min         4.565
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    1.327
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.719
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
 CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021) Numerical 
 absorption correction based on gaussian integration over a multifaceted 
 crystal model Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_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          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3034
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0288
_refine_ls_R_factor_gt           0.0285
_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^)+(0.0395P)^2^+0.3155P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0783
_refine_ls_wR_factor_ref         0.0786
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2980
_reflns_number_total             3034
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc01500f2.cif
_cod_data_source_block           1-OTMS
_cod_depositor_comments
'Adding full bibliography for 1574244--1574256.cif.'
_cod_database_code               1574251
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.777
_shelx_estimated_absorpt_t_max   0.890
_shelx_res_checksum              99161