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_1574254
_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         'C25 H20 B N2, C16 H36 N'
_chemical_formula_sum            'C41 H56 B N3'
_chemical_formula_weight         601.69
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2024-10-28
_audit_creation_method           'CIF-fill 1.5k (K.Radacki, 2005-24)'
_audit_update_record
;
2024-10-28 deposited with the CCDC.	2025-03-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.5390(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.26330(10)
_cell_length_b                   17.39660(10)
_cell_length_c                   16.9860(2)
_cell_measurement_reflns_used    30113
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.7260
_cell_measurement_theta_min      4.5060
_cell_volume                     3491.33(6)
_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 0.998
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w     30.00  56.00   0.50    0.05    --   18.00  60.00 -46.08   52
  2  \w     30.00  56.00   0.50    0.05    --   18.00  60.00  -0.59   52
  3  \w     34.00  60.00   0.50    0.05    --   22.00  58.00 -92.61   52
  4  \w     34.00  60.00   0.50    0.05    --   22.00  57.00-143.75   52
  5  \w     34.00  60.00   0.50    0.05    --   22.00  58.00  45.19   52
  6  \w     30.00  60.00   0.50    0.05    --   18.00  59.00 132.41   60
  7  \w     34.00  60.00   0.50    0.05    --   22.00  57.00  93.38   52
  8  \w     46.00 133.00   0.50    0.05    --   82.26  15.00 120.00  174
  9  \w     24.00  99.00   0.50    0.05    --   71.44-126.00 150.00  150
 10  \w     40.00  90.00   0.50    0.05    --   82.26 -95.00   0.00  100
 11  \w     40.00  90.00   0.50    0.05    --   82.26 -95.00  90.00  100
 12  \w     40.00  90.00   0.50    0.05    --   82.26 -95.00 120.00  100
 13  \w     40.00  90.00   0.50    0.05    --   82.26 -95.00 150.00  100
 14  \w     40.00  90.00   0.50    0.05    --   82.26 -95.00 -30.00  100
 15  \w     40.00  90.00   0.50    0.05    --   82.26 -95.00 -60.00  100
 16  \w     40.00  90.00   0.50    0.05    --   82.26 -95.00 -90.00  100
 17  \w     40.00  90.00   0.50    0.05    --   82.26 -95.00-120.00  100
 18  \w     42.00  93.00   0.50    0.05    --   85.25 -97.00-140.49  102
 19  \w     37.00  93.00   0.50    0.05    --   82.26-112.00-180.00  112
 20  \w     40.00  90.00   0.50    0.05    --   82.26 -95.00  30.00  100
 21  \w     46.00 133.00   0.50    0.05    --   82.26  15.00 -60.00  174
 22  \w     -5.00  21.00   0.50    0.05    --  -10.00  77.00 -85.37   52
 23  \w    -97.00 -33.00   0.50    0.05    --  -79.50 115.00-134.20  128
 24  \w    -97.00 -32.00   0.50    0.05    --  -78.00 114.00 -50.19  130
 25  \w    -96.00 -34.00   0.50    0.05    --  -79.50 114.00  12.64  124
 26  \w    -97.00 -32.00   0.50    0.05    --  -78.00 114.00 139.85  130
 27  \w    -92.00 -31.00   0.50    0.05    --  -76.36 112.00  60.00  122
 28  \w    -92.00 -31.00   0.50    0.05    --  -76.36 112.00 -30.00  122
 29  \w    -92.00 -35.00   0.50    0.05    --  -79.50 102.00 -92.85  114
 30  \w    -92.00 -31.00   0.50    0.05    --  -76.36 112.00-180.00  122
 31  \w    -94.00 -59.00   0.50    0.05    --  -46.00 -51.00-179.47   70
 32  \w   -125.00 -90.00   0.50    0.05    --  -79.50 -62.00-135.66   70
 33  \w   -100.00 -62.00   0.50    0.05    --  -50.00 -41.00  28.10   76
 34  \w   -120.00 -86.00   0.50    0.05    --  -74.00 -59.00 -31.29   68
 35  \w   -125.00 -91.00   0.50    0.05    --  -79.50 -60.00  41.68   68
 36  \w   -120.00 -86.00   0.50    0.05    --  -74.00 -59.00 -63.58   68
 37  \w   -126.00 -91.00   0.50    0.05    --  -79.50 -58.00-114.30   70
 38  \w   -121.00 -86.00   0.50    0.05    --  -74.00 -58.00 -96.66   70
 39  \w   -125.00 -90.00   0.50    0.05    --  -78.00 -57.00 -11.63   70
 40  \w   -120.00 -86.00   0.50    0.05    --  -74.00 -59.00  55.91   68
 41  \w    -79.00 -44.00   0.50    0.05    --  -30.00 -49.00 120.21   70
 42  \w   -125.00 -90.00   0.50    0.05    --  -78.00 -55.00 169.35   70
 43  \w   -120.00 -86.00   0.50    0.05    --  -74.00 -60.00 133.45   68
 44  \w   -106.00 -71.00   0.50    0.05    --  -58.00 -52.00 103.63   70
 45  \w   -122.00 -87.00   0.50    0.05    --  -74.00 -53.00  96.62   70
 46  \w   -128.00 -93.00   0.50    0.05    --  -79.50 -50.00  86.38   70
 47  \w   -110.00 -75.00   0.50    0.05    --  -62.00 -51.00 -74.41   70
 48  \w   -110.00 -75.00   0.50    0.05    --  -62.00 -52.00-136.62   70
 49  \w   -128.00 -93.00   0.50    0.05    --  -79.50 -51.00 -84.10   70
 50  \w   -128.00 -93.00   0.50    0.05    --  -79.50 -50.00 -45.86   70
 51  \w   -107.00 -72.00   0.50    0.05    --  -58.00 -48.00 -33.37   70
 52  \w   -103.00 -67.00   0.50    0.05    --  -54.00 -46.00  -5.62   72
 53  \w   -129.00 -93.00   0.50    0.05    --  -79.50 -46.00   1.56   72
 54  \w   -129.00 -93.00   0.50    0.05    --  -79.50 -48.00  62.47   72
 55  \w   -115.00 -80.00   0.50    0.05    --  -66.00 -47.00 134.77   70
 56  \w   -120.00 -83.00   0.50    0.05    --  -70.00 -46.00 177.56   74
 57  \w   -130.00 -92.00   0.50    0.05    --  -79.50 -42.00 132.69   76
 58  \w   -127.00 -90.00   0.50    0.05    --  -79.50-127.00  63.45   74
 59  \w   -126.00 -92.00   0.50    0.05    --  -79.50-122.00 170.59   68
 60  \w   -126.00 -92.00   0.50    0.05    --  -79.50-123.00 108.80   68
 61  \w   -126.00 -93.00   0.50    0.05    --  -79.50-120.00 115.71   66
 62  \w   -127.00 -90.00   0.50    0.05    --  -79.50-126.00  32.38   74
 63  \w   -125.00 -94.00   0.50    0.05    --  -79.50-119.00 -13.78   62
 64  \w   -126.00 -92.00   0.50    0.05    --  -79.50-123.00 -31.36   68
 65  \w   -125.00 -94.00   0.50    0.05    --  -79.50-119.00 -75.04   62
 66  \w   -126.00 -93.00   0.50    0.05    --  -79.50-121.00-101.01   66
 67  \w   -126.00 -93.00   0.50    0.05    --  -79.50-121.00-128.53   66
 68  \w   -126.00 -93.00   0.50    0.05    --  -79.50-120.00-158.26   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      0.0845216000
_diffrn_orient_matrix_UB_12      -0.0370629000
_diffrn_orient_matrix_UB_13      0.0740476000
_diffrn_orient_matrix_UB_21      -0.0907648000
_diffrn_orient_matrix_UB_22      0.0010926000
_diffrn_orient_matrix_UB_23      0.0475480000
_diffrn_orient_matrix_UB_31      -0.0401925000
_diffrn_orient_matrix_UB_32      -0.0804297000
_diffrn_orient_matrix_UB_33      -0.0334278000
_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  0.0494
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            38740
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.723
_diffrn_reflns_theta_min         4.524
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    0.491
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.222
_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    1.145
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_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          0.670
_exptl_crystal_size_mid          0.390
_exptl_crystal_size_min          0.270
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         3501
_refine_ls_number_restraints     1321
_refine_ls_restrained_S_all      0.951
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0414
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0474P)^2^+1.9229P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1046
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3345
_reflns_number_total             3501
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc01500f2.cif
_cod_data_source_block           2-TBA
_cod_depositor_comments
'Adding full bibliography for 1574244--1574256.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1574254
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.735
_shelx_estimated_absorpt_t_max   0.879
_shelx_res_checksum              62307