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_1574248
_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         'C19 H15 B F N2, C16 H36 N'
_chemical_formula_sum            'C35 H51 B F N3'
_chemical_formula_weight         543.59
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2024-05-08
_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                 97.1460(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.81050(10)
_cell_length_b                   16.1727(2)
_cell_length_c                   20.3437(3)
_cell_measurement_reflns_used    26924
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.6810
_cell_measurement_theta_min      3.4830
_cell_volume                     3202.71(7)
_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 0.994
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w     17.00  65.00   0.50    0.79    --   58.44 -93.00 159.00   96
  2  \w    -66.00 -18.00   0.50    0.79    --  -60.13  93.00 -88.00   96
  3  \w    -75.00 -27.00   0.50    0.79    --  -69.55  93.00 -88.00   96
  4  \w     29.00  77.00   0.50    0.79    --   71.24 -93.00 159.00   96
  5  \w    -82.00 -34.00   0.50    0.79    --  -76.36  93.00 -88.00   96
  6  \w     40.00  88.00   0.50    0.79    --   82.26 -93.00 159.00   96
  7  \w     48.00  83.00   0.50    0.79    --   34.00  51.00 156.18   70
  8  \w    -91.00 -55.00   0.50    0.79    --  -42.00 -46.00 -35.75   72
  9  \w    -94.00 -59.00   0.50    0.79    --  -46.00 -51.00-148.83   70
 10  \w   -107.00 -72.00   0.50    0.79    --  -58.00 -49.00  46.58   70
 11  \w     16.00  66.00   0.50    0.79    --   58.44 -95.00 -30.00  100
 12  \w   -110.00 -75.00   0.50    0.79    --  -62.00 -51.00  94.19   70
 13  \w   -114.00 -79.00   0.50    0.79    --  -66.00 -51.00-167.75   70
 14  \w   -120.00 -83.00   0.50    0.79    --  -70.00 -46.00 130.80   74
 15  \w   -117.00 -85.00   0.50    0.79    --  -70.00 -58.00 -94.57   64
 16  \w   -121.00 -86.00   0.50    0.79    --  -74.00 -58.00 165.65   70
 17  \w   -124.00 -86.00   0.50    0.79    --  -74.00 -42.00-162.07   76
 18  \w   -122.00 -87.00   0.50    0.79    --  -74.00 -51.00  24.73   70
 19  \w    -92.00 -31.00   0.50    0.79    --  -76.36 112.00  60.00  122
 20  \w   -130.00 -72.00   0.50    0.79    --  -78.00 -22.00 -38.72  116
 21  \w    -97.00 -32.00   0.50    0.79    --  -78.00 114.00 -25.17  130
 22  \w   -130.00 -92.00   0.50    0.79    --  -79.50 -42.00 -53.81   76
 23  \w   -128.00 -93.00   0.50    0.79    --  -79.50 -50.00 105.03   70
 24  \w   -125.00 -91.00   0.50    0.79    --  -79.50 -60.00 -16.10   68
 25  \w   -126.00 -92.00   0.50    0.79    --  -79.50-123.00 117.04   68
 26  \w   -126.00 -91.00   0.50    0.79    --  -79.50 -59.00  69.20   70
 27  \w   -130.00 -91.00   0.50    0.79    --  -79.50 -39.00 141.33   78
 28  \w   -126.00 -93.00   0.50    0.79    --  -79.50-120.00 -41.76   66
 29  \w   -126.00 -92.00   0.50    0.79    --  -79.50-122.00-118.58   68
 30  \w   -130.00 -91.00   0.50    0.79    --  -79.50 -41.00 160.11   78
 31  \w   -124.00 -92.00   0.50    0.79    --  -79.50 -63.00-112.44   64
 32  \w   -125.00 -91.00   0.50    0.79    --  -79.50 -60.00-142.11   68
 33  \w   -107.00 -33.00   0.50    0.79    --  -79.50 137.00 142.84  148
 34  \w   -129.00 -93.00   0.50    0.79    --  -79.50 -47.00  90.07   72
 35  \w   -126.00 -92.00   0.50    0.79    --  -79.50-123.00 173.29   68
 36  \w   -127.00 -90.00   0.50    0.79    --  -79.50-127.00 -87.81   74
 37  \w    -97.00 -33.00   0.50    0.79    --  -79.50 115.00  80.64  128
 38  \w     40.00  90.00   0.50    0.79    --   82.26 -95.00 -90.00  100
 39  \w     46.00 133.00   0.50    0.79    --   82.26  15.00   0.00  174
 40  \w     40.00  90.00   0.50    0.79    --   82.26 -95.00 -60.00  100
 41  \w     40.00  90.00   0.50    0.79    --   82.26 -95.00   0.00  100
 42  \w     40.00  90.00   0.50    0.79    --   82.26 -95.00-120.00  100
 43  \w     37.00  93.00   0.50    0.79    --   82.26-112.00  90.00  112
 44  \w     37.00  93.00   0.50    0.79    --   82.26-112.00-120.00  112
 45  \w     40.00  90.00   0.50    0.79    --   82.26 -95.00  60.00  100
 46  \w     40.00  90.00   0.50    0.79    --   82.26 -95.00 150.00  100
 47  \w     40.00  90.00   0.50    0.79    --   82.26 -95.00  90.00  100
 48  \w     40.00  90.00   0.50    0.79    --   82.26 -95.00 -30.00  100
 49  \w     40.00  90.00   0.50    0.79    --   82.26 -95.00-180.00  100
 50  \w     42.00  93.00   0.50    0.79    --   85.25 -98.00  61.74  102
 51  \w     42.00  92.00   0.50    0.79    --   85.25 -99.00  27.25  100
 52  \w     42.00  93.00   0.50    0.79    --   85.25 -98.00 -38.12  102
 53  \w     25.00  54.00   0.50    0.79    --   14.00  61.00 -95.02   58
 54  \w     25.00  54.00   0.50    0.79    --   14.00  61.00  38.57   58
 55  \w     34.00  60.00   0.50    0.79    --   22.00  59.00  71.02   52
 56  \w     34.00  60.00   0.50    0.79    --   22.00  59.00 158.76   52
 57  \w     34.00  60.00   0.50    0.79    --   22.00  57.00 125.31   52
 58  \w     34.00  60.00   0.50    0.79    --   22.00  57.00-153.86   52
 59  \w    -87.00 -52.00   0.50    0.79    --  -38.00 -48.00-115.49   70
 60  \w    -86.00 -51.00   0.50    0.79    --  -38.00 -52.00 -70.26   70
 61  \w   -120.00 -88.00   0.50    0.79    --  -74.00 -59.00   0.16   64
 62  \w   -120.00 -86.00   0.50    0.79    --  -74.00 -60.00  45.68   68
 63  \w   -121.00 -86.00   0.50    0.79    --  -74.00 -55.00  81.95   70
 64  \w   -123.00 -87.00   0.50    0.79    --  -74.00 -46.00 -84.31   72
 65  \w   -121.00 -86.00   0.50    0.79    --  -74.00 -55.00 126.14   70
 66  \w   -122.00 -87.00   0.50    0.79    --  -74.00 -54.00-173.60   70
 67  \w   -126.00 -93.00   0.50    0.79    --  -79.50-120.00 -68.36   66
 68  \w   -127.00 -90.00   0.50    0.79    --  -79.50-126.00  60.60   74
 69  \w   -126.00 -92.00   0.50    0.79    --  -79.50-122.00  86.02   68
 70  \w   -126.00 -92.00   0.50    0.79    --  -79.50-123.00-162.36   68
;
_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      0.0669020000
_diffrn_orient_matrix_UB_12      -0.0543361000
_diffrn_orient_matrix_UB_13      0.0573630000
_diffrn_orient_matrix_UB_21      0.0408188000
_diffrn_orient_matrix_UB_22      0.0781699000
_diffrn_orient_matrix_UB_23      0.0410130000
_diffrn_orient_matrix_UB_31      -0.1374553000
_diffrn_orient_matrix_UB_32      -0.0032762000
_diffrn_orient_matrix_UB_33      0.0292195000
_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  0.0478
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            72923
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.085
_diffrn_reflns_theta_min         3.502
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    0.529
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.685
_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    1.127
_exptl_crystal_description       plate
_exptl_crystal_F_000             1184
_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          0.210
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     519
_refine_ls_number_reflns         6364
_refine_ls_number_restraints     780
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0481
_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^)+(0.0455P)^2^+1.3475P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1150
_refine_ls_wR_factor_ref         0.1205
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5317
_reflns_number_total             6364
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc01500f2.cif
_cod_data_source_block           3-F
_cod_depositor_comments
'Adding full bibliography for 1574244--1574256.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1574248
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.897
_shelx_estimated_absorpt_t_max   0.979
_shelx_res_checksum              91702