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_1574244
_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         'C20 H14 B F3 N2'
_chemical_formula_sum            'C20 H14 B F3 N2'
_chemical_formula_weight         350.14
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2024-05-06
_audit_creation_method           'CIF-fill 1.4y (K.Radacki, 2005-23)'
_audit_update_record
;
2024-10-28 deposited with the CCDC.	2025-03-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.1650(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.46310(10)
_cell_length_b                   9.34580(10)
_cell_length_c                   15.17920(10)
_cell_measurement_reflns_used    44006
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.9950
_cell_measurement_theta_min      3.7570
_cell_volume                     3333.17(5)
_computing_cell_refinement       'CrysAlisPro 1.171.43.111a (Rigaku OD, 2024)'
_computing_data_collection
;
 CrysAlisPro system (CCD 43.119a 64-bit (release 08-04-2024))
;
_computing_data_reduction        'CrysAlisPro 1.171.43.111a (Rigaku OD, 2024)'
_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 0.997
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w     15.00  43.00   0.50    0.44    --    2.00  64.00 168.03   56
  2  \w   -128.00 -94.00   0.50    0.44    --  -79.50 -41.00 129.37   68
  3  \w     28.00  54.00   0.50    0.44    --   14.00  61.00  12.47   52
  4  \w   -128.00 -94.00   0.50    0.44    --  -79.50 -42.00 151.58   68
  5  \w     62.00  92.00   0.50    0.44    --   46.00  52.00  19.44   60
  6  \w   -123.00 -88.00   0.50    0.44    --  -74.00 -36.00 -88.30   70
  7  \w   -128.00 -94.00   0.50    0.44    --  -79.50 -41.00  89.63   68
  8  \w     54.00  84.00   0.50    0.44    --   38.00  52.00  70.03   60
  9  \w     28.00  54.00   0.50    0.44    --   14.00  61.00  71.09   52
 10  \w   -128.00 -94.00   0.50    0.44    --  -79.50 -41.00  76.97   68
 11  \w   -119.00 -84.00   0.50    0.44    --  -70.00 -40.00  90.28   70
 12  \w     58.00  89.00   0.50    0.44    --   42.00  51.00-104.14   62
 13  \w   -128.00 -94.00   0.50    0.44    --  -79.50 -42.00 -56.13   68
 14  \w   -105.00 -74.00   0.50    0.44    --  -58.00 -49.00  23.43   62
 15  \w   -110.00 -77.00   0.50    0.44    --  -62.00 -44.00  48.57   66
 16  \w   -114.00 -82.00   0.50    0.44    --  -66.00 -46.00 126.26   64
 17  \w     54.00  85.00   0.50    0.44    --   38.00  51.00-137.81   62
 18  \w    -97.00 -36.00   0.50    0.44    --  -79.50 115.00-106.33  122
 19  \w    -97.00 -36.00   0.50    0.44    --  -79.50 114.00  13.44  122
 20  \w    -33.00  -4.00   0.50    0.44    --  -18.00 110.00  -8.30   58
 21  \w   -120.00 -89.00   0.50    0.44    --  -74.00 -54.00 -26.14   62
 22  \w   -123.00 -93.00   0.50    0.44    --  -79.50 -61.00  76.59   60
 23  \w   -125.00 -90.00   0.50    0.44    --  -79.50-126.00 -42.98   70
 24  \w    -97.00 -36.00   0.50    0.44    --  -79.50 114.00 -32.47  122
 25  \w    -92.00 -33.00   0.50    0.44    --  -76.32 112.00   0.00  118
 26  \w   -120.00 -89.00   0.50    0.44    --  -74.00 -53.00  16.93   62
 27  \w    -98.00 -34.00   0.50    0.44    --  -79.50 120.00 101.44  128
 28  \w   -120.00 -89.00   0.50    0.44    --  -74.00 -54.00-157.50   62
 29  \w   -116.00 -85.00   0.50    0.44    --  -70.00 -52.00 -59.95   62
 30  \w    -92.00 -33.00   0.50    0.44    --  -76.32 112.00 -30.00  118
 31  \w   -106.00 -35.00   0.50    0.44    --  -79.50 136.00 -97.15  142
 32  \w    -97.00 -35.00   0.50    0.44    --  -79.50 116.00-117.74  124
 33  \w   -128.00 -93.00   0.50    0.44    --  -79.50 -39.00-149.03   70
 34  \w    -97.00 -36.00   0.50    0.44    --  -79.50 115.00 -73.57  122
 35  \w   -105.00 -74.00   0.50    0.44    --  -58.00 -47.00 -46.30   62
 36  \w    -92.00 -33.00   0.50    0.44    --  -76.32 112.00 150.00  118
 37  \w    -54.00 -28.00   0.50    0.44    --  -14.00 -58.00 170.23   52
 38  \w     19.00  66.00   0.50    0.44    --   60.18 -95.00-150.00   94
 39  \w   -125.00 -90.00   0.50    0.44    --  -79.50-126.00 166.35   70
 40  \w   -125.00 -90.00   0.50    0.44    --  -79.50-126.00 -65.43   70
 41  \w     40.00  86.00   0.50    0.44    --   80.28 -95.00  60.00   92
 42  \w   -128.00 -67.00   0.50    0.44    --  -79.50 -18.00  -9.47  122
 43  \w    -97.00 -36.00   0.50    0.44    --  -79.50 115.00  93.89  122
 44  \w     62.00  92.00   0.50    0.44    --   46.00  52.00 -87.64   60
 45  \w   -105.00 -74.00   0.50    0.44    --  -58.00 -49.00 147.87   62
 46  \w     32.00  60.00   0.50    0.44    --   18.00  59.00 -28.42   56
 47  \w     50.00  81.00   0.50    0.44    --   34.00  51.00 112.76   62
 48  \w   -125.00 -90.00   0.50    0.44    --  -79.50-126.00  35.38   70
 49  \w     19.00  66.00   0.50    0.44    --   60.18 -95.00 120.00   94
 50  \w   -125.00 -90.00   0.50    0.44    --  -79.50-126.00  55.02   70
 51  \w    -97.00 -36.00   0.50    0.44    --  -79.50 114.00-155.99  122
 52  \w   -125.00 -90.00   0.50    0.44    --  -79.50-126.00-115.20   70
 53  \w     40.00  86.00   0.50    0.44    --   80.28 -95.00   0.00   92
 54  \w   -125.00 -94.00   0.50    0.44    --  -79.50 -53.00 -81.38   62
 55  \w    -97.00 -36.00   0.50    0.44    --  -79.50 114.00  59.78  122
 56  \w     42.00  91.00   0.50    0.44    --   83.50 -99.00 -69.04   98
 57  \w     41.00  92.00   0.50    0.44    --   83.50-104.00 166.17  102
 58  \w   -119.00 -83.00   0.50    0.44    --  -70.00 -35.00 154.90   72
 59  \w    -98.00 -34.00   0.50    0.44    --  -79.50 120.00 165.30  128
 60  \w     42.00  73.00   0.50    0.44    --   26.00  51.00-166.65   62
 61  \w   -122.00 -89.00   0.50    0.44    --  -74.00 -42.00-114.28   66
 62  \w    -97.00 -36.00   0.50    0.44    --  -79.50 115.00 136.30  122
 63  \w   -126.00 -96.00   0.50    0.44    --  -79.50 -49.00   2.08   60
 64  \w   -123.00 -93.00   0.50    0.44    --  -79.50 -62.00  63.96   60
 65  \w   -118.00 -88.00   0.50    0.44    --  -74.00 -61.00-111.49   60
 66  \w    -97.00 -36.00   0.50    0.44    --  -79.50 114.00  67.49  122
 67  \w   -119.00 -88.00   0.50    0.44    --  -74.00 -57.00  -4.45   62
 68  \w   -124.00 -91.00   0.50    0.44    --  -79.50-124.00  78.58   66
 69  \w   -124.00 -91.00   0.50    0.44    --  -79.50-124.00 111.22   66
;
_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      -0.0102689000
_diffrn_orient_matrix_UB_12      0.1618529000
_diffrn_orient_matrix_UB_13      -0.0156718000
_diffrn_orient_matrix_UB_21      0.0205533000
_diffrn_orient_matrix_UB_22      0.0253883000
_diffrn_orient_matrix_UB_23      0.1042949000
_diffrn_orient_matrix_UB_31      0.0614166000
_diffrn_orient_matrix_UB_32      0.0186345000
_diffrn_orient_matrix_UB_33      -0.0060771000
_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  0.0357
_diffrn_reflns_av_unetI/netI     0.0120
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            76152
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.142
_diffrn_reflns_theta_min         3.763
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    0.885
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.623
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
 CrysAlisPro 1.171.43.111a (Rigaku Oxford Diffraction, 2024) 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            colourless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_description       needle
_exptl_crystal_F_000             1440
_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          0.460
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     500
_refine_ls_number_reflns         6654
_refine_ls_number_restraints     193
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0335
_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^)+(0.0461P)^2^+1.2531P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0875
_refine_ls_wR_factor_ref         0.0892
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6206
_reflns_number_total             6654
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc01500f2.cif
_cod_data_source_block           1-CF3
_cod_depositor_comments
'Adding full bibliography for 1574244--1574256.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1574244
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.686
_shelx_estimated_absorpt_t_max   0.933
_shelx_res_checksum              61863