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_1574250
_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 H17 B N2 O'
_chemical_formula_sum            'C20 H17 B N2 O'
_chemical_formula_weight         312.16
_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             2024-05-27
_audit_creation_method           'CIF-fill 1.5c (K.Radacki, 2005-23)'
_audit_update_record
;
2024-10-28 deposited with the CCDC.	2025-03-18 downloaded from the CCDC.
;
_cell_angle_alpha                106.0570(10)
_cell_angle_beta                 93.7340(10)
_cell_angle_gamma                100.512(2)
_cell_formula_units_Z            2
_cell_length_a                   6.52650(10)
_cell_length_b                   9.4226(2)
_cell_length_c                   14.2267(2)
_cell_measurement_reflns_used    11237
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.4170
_cell_measurement_theta_min      3.2520
_cell_volume                     820.44(3)
_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 0.993
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w     40.00  90.00   0.50    0.05    --   82.26 -95.00 -60.00  100
  2  \w     40.00  90.00   0.50    0.05    --   82.26 -95.00-180.00  100
  3  \w     40.00  90.00   0.50    0.05    --   82.26 -95.00-150.00  100
  4  \w     46.00 133.00   0.50    0.05    --   82.26  15.00-150.00  174
  5  \w     46.00 133.00   0.50    0.05    --   82.26  15.00 -90.00  174
  6  \w     46.00 133.00   0.50    0.05    --   82.26  15.00-150.00  174
  7  \w   -118.00 -83.00   0.50    0.05    --  -70.00 -53.00 -65.02   70
  8  \w   -130.00 -91.00   0.50    0.05    --  -79.50 -39.00-103.45   78
  9  \w   -122.00 -87.00   0.50    0.05    --  -74.00 -52.00-152.80   70
 10  \w   -126.00 -91.00   0.50    0.05    --  -79.50 -59.00  91.95   70
 11  \w   -107.00 -72.00   0.50    0.05    --  -58.00 -50.00-132.88   70
 12  \w   -125.00 -91.00   0.50    0.05    --  -79.50 -61.00 150.96   68
 13  \w   -121.00 -86.00   0.50    0.05    --  -74.00 -57.00  99.97   70
 14  \w   -124.00 -89.00   0.50    0.05    --  -78.00 -60.00 120.41   70
 15  \w   -125.00 -90.00   0.50    0.05    --  -78.00 -55.00  51.82   70
 16  \w   -122.00 -87.00   0.50    0.05    --  -74.00 -51.00 156.17   70
 17  \w     46.00 133.00   0.50    0.05    --   82.26  15.00  60.00  174
 18  \w     46.00 133.00   0.50    0.05    --   82.26  15.00 -30.00  174
 19  \w    -92.00 -31.00   0.50    0.05    --  -76.36 112.00  60.00  122
 20  \w   -127.00 -92.00   0.50    0.05    --  -79.50 -55.00  13.76   70
 21  \w    -92.00 -31.00   0.50    0.05    --  -76.36 112.00-120.00  122
 22  \w   -126.00 -93.00   0.50    0.05    --  -79.50-121.00-164.31   66
 23  \w    -97.00 -32.00   0.50    0.05    --  -78.00 114.00 -13.85  130
 24  \w    -92.00 -31.00   0.50    0.05    --  -76.36 112.00 120.00  122
 25  \w   -126.00 -91.00   0.50    0.05    --  -79.50 -59.00-131.38   70
 26  \w    -92.00 -31.00   0.50    0.05    --  -76.36 112.00  30.00  122
 27  \w    -48.00 -21.00   0.50    0.05    --  -14.00 136.00  -4.12   54
 28  \w    -92.00 -42.00   0.50    0.05    --  -76.36 112.00 150.00  100
 29  \w     30.00  56.00   0.50    0.05    --   18.00  60.00  96.13   52
 30  \w    -92.00 -31.00   0.50    0.05    --  -76.36 112.00 120.00  122
 31  \w    -97.00 -32.00   0.50    0.05    --  -78.00 114.00 -45.64  130
 32  \w   -125.00 -91.00   0.50    0.05    --  -79.50 -61.00-177.06   68
 33  \w    -92.00 -31.00   0.50    0.05    --  -76.36 112.00-180.00  122
 34  \w   -125.00 -91.00   0.50    0.05    --  -79.50 -60.00-162.45   68
 35  \w     40.00  90.00   0.50    0.05    --   82.26 -95.00 150.00  100
 36  \w    -92.00 -31.00   0.50    0.05    --  -76.36 112.00  90.00  122
 37  \w     40.00  90.00   0.50    0.05    --   82.26 -95.00 -30.00  100
 38  \w   -111.00 -76.00   0.50    0.05    --  -62.00 -48.00 107.33   70
 39  \w     16.00  66.00   0.50    0.05    --   58.74 -95.00 -60.00  100
 40  \w   -110.00 -75.00   0.50    0.05    --  -62.00 -51.00 -41.61   70
 41  \w   -126.00 -92.00   0.50    0.05    --  -79.50-122.00 117.93   68
 42  \w     40.00  90.00   0.50    0.05    --   82.26 -95.00 -90.00  100
 43  \w   -127.00 -92.00   0.50    0.05    --  -79.50 -54.00 -75.11   70
 44  \w   -107.00 -72.00   0.50    0.05    --  -58.00 -50.00  10.45   70
 45  \w     46.00 133.00   0.50    0.05    --   82.26  15.00  60.00  174
 46  \w     30.00  56.00   0.50    0.05    --   18.00  60.00-148.96   52
 47  \w     34.00  60.00   0.50    0.05    --   22.00  58.00 171.40   52
 48  \w     38.00 122.00   0.50    0.05    --   71.44  15.00 120.00  168
 49  \w   -118.00 -83.00   0.50    0.05    --  -70.00 -54.00  -4.71   70
 50  \w     30.00  56.00   0.50    0.05    --   18.00  60.00  10.52   52
 51  \w   -126.00 -93.00   0.50    0.05    --  -79.50-120.00  88.88   66
 52  \w   -126.00 -93.00   0.50    0.05    --  -79.50-121.00 169.89   66
 53  \w     38.00 122.00   0.50    0.05    --   71.44  15.00 120.00  168
 54  \w     30.00  60.00   0.50    0.05    --   18.00  59.00 -72.22   60
 55  \w     40.00  90.00   0.50    0.05    --   82.26 -95.00  90.00  100
 56  \w   -126.00 -93.00   0.50    0.05    --  -79.50-120.00  22.77   66
 57  \w     40.00  90.00   0.50    0.05    --   82.26 -95.00  60.00  100
 58  \w     40.00  90.00   0.50    0.05    --   82.26 -95.00 120.00  100
 59  \w   -111.00 -76.00   0.50    0.05    --  -62.00 -48.00  50.40   70
;
_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      -0.1928817000
_diffrn_orient_matrix_UB_12      -0.0473767000
_diffrn_orient_matrix_UB_13      -0.0787346000
_diffrn_orient_matrix_UB_21      -0.0167884000
_diffrn_orient_matrix_UB_22      -0.1660070000
_diffrn_orient_matrix_UB_23      -0.0018893000
_diffrn_orient_matrix_UB_31      -0.1450056000
_diffrn_orient_matrix_UB_32      0.0215701000
_diffrn_orient_matrix_UB_33      0.0817777000
_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  0.0497
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19256
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.840
_diffrn_reflns_theta_min         3.257
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    0.610
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.686
_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    1.264
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_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          0.260
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3202
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0438
_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^)+(0.0721P)^2^+0.1522P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1247
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2811
_reflns_number_total             3202
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc01500f2.cif
_cod_data_source_block           1-OMe
_cod_depositor_comments
'Adding full bibliography for 1574244--1574256.cif.'
_cod_database_code               1574250
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.858
_shelx_estimated_absorpt_t_max   0.942
_shelx_res_checksum              25511