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_1574246
_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         'C23 H23 B N2'
_chemical_formula_sum            'C23 H23 B N2'
_chemical_formula_weight         338.24
_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             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                90
_cell_angle_beta                 104.0560(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.59790(10)
_cell_length_b                   15.3284(2)
_cell_length_c                   11.92880(10)
_cell_measurement_reflns_used    24495
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.0340
_cell_measurement_theta_min      2.8710
_cell_volume                     1879.80(4)
_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 0.995
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w     59.00  84.00   0.50    0.05    --   46.00  52.00 162.32   50
  2  \w     62.00  87.00   0.50    0.05    --   46.00  52.00  14.20   50
  3  \w     47.00  72.00   0.50    0.05    --   34.00  52.00 -35.96   50
  4  \w     53.00  84.00   0.50    0.05    --   38.00  50.00 -10.25   62
  5  \w    102.00 128.00   0.50    0.05    --   80.79  45.00   8.60   52
  6  \w     24.00  90.00   0.50    0.05    --   58.57-132.00 -42.00  132
  7  \w     30.00 103.00   0.50    0.05    --   76.90-132.00 -42.00  146
  8  \w     25.00 102.00   0.50    0.05    --   71.34-132.00 -42.00  154
  9  \w     46.00  71.00   0.50    0.05    --   84.69-132.00 -42.00   50
 10  \w     35.00  65.00   0.50    0.05    --   80.79-114.00-177.13   60
 11  \w     29.00  94.00   0.50    0.05    --   58.57-139.00 142.00  130
 12  \w     31.00 109.00   0.50    0.05    --   76.90-139.00 142.00  156
 13  \w     39.00 108.00   0.50    0.05    --   84.69-139.00 142.00  138
 14  \w     49.00  92.00   0.50    0.05    --   80.79-100.00 139.10   86
 15  \w     45.00  92.00   0.50    0.05    --   84.69 -95.00  30.00   94
 16  \w     48.00  92.00   0.50    0.05    --   84.69 -95.00   0.00   88
 17  \w     34.00  81.00   0.50    0.05    --   76.90 -95.00 -30.00   94
 18  \w     52.00  91.00   0.50    0.05    --   84.69 -95.00 -60.00   78
 19  \w     42.00  91.00   0.50    0.05    --   84.69 -95.00-120.00   98
 20  \w     56.00  92.00   0.50    0.05    --   84.69 -95.00-180.00   72
 21  \w     42.00  91.00   0.50    0.05    --   84.69 -95.00 -90.00   98
 22  \w     45.00  90.00   0.50    0.05    --   84.69 -95.00  60.00   90
 23  \w     58.00  92.00   0.50    0.05    --   84.69 -95.00  90.00   68
 24  \w     96.00 128.00   0.50    0.05    --   80.79  49.00-121.10   64
 25  \w    -96.00 -23.00   0.50    0.05    --  -60.16 139.00-157.00  146
 26  \w   -105.00 -24.00   0.50    0.05    --  -69.76 139.00-157.00  162
 27  \w   -108.00 -30.00   0.50    0.05    --  -76.35 139.00-157.00  156
 28  \w    -97.00 -35.00   0.50    0.05    --  -79.50 116.00 -14.52  124
 29  \w   -101.00 -23.00   0.50    0.05    --  -69.76 132.00  27.00  156
 30  \w    -91.00 -18.00   0.50    0.05    --  -60.16 132.00  27.00  146
 31  \w   -102.00 -29.00   0.50    0.05    --  -76.35 132.00  27.00  146
 32  \w    -92.00 -32.00   0.50    0.05    --  -76.35 112.00 150.00  120
 33  \w   -123.00 -92.00   0.50    0.05    --  -79.50 -63.00 101.99   62
 34  \w   -122.00 -90.00   0.50    0.05    --  -79.50 -62.00 122.35   64
 35  \w   -115.00 -86.00   0.50    0.05    --  -70.00 -59.00  32.46   58
 36  \w   -120.00 -92.00   0.50    0.05    --  -74.00 -55.00   1.44   56
 37  \w   -125.00-100.00   0.50    0.05    --  -79.50 -61.00   0.89   50
 38  \w   -126.00 -94.00   0.50    0.05    --  -79.50 -53.00 125.77   64
 39  \w   -121.00 -95.00   0.50    0.05    --  -74.00 -55.00 137.71   52
 40  \w   -125.00 -93.00   0.50    0.05    --  -79.50 -52.00  48.45   64
 41  \w   -120.00 -87.00   0.50    0.05    --  -74.00 -56.00 -67.92   66
 42  \w   -106.00 -81.00   0.50    0.05    --  -58.00 -51.00 -50.48   50
 43  \w   -116.00 -90.00   0.50    0.05    --  -70.00 -56.00-139.78   52
 44  \w   -125.00 -93.00   0.50    0.05    --  -79.50 -61.00-168.52   64
 45  \w   -128.00 -98.00   0.50    0.05    --  -79.50 -51.00 -38.38   60
 46  \w   -101.00 -72.00   0.50    0.05    --  -58.00 -48.00-153.65   58
 47  \w   -107.00 -73.00   0.50    0.05    --  -58.00 -49.00  51.78   68
 48  \w   -130.00-105.00   0.50    0.05    --  -79.50 -40.00 -78.97   50
 49  \w   -108.00 -80.00   0.50    0.05    --  -66.00 -44.00 136.09   56
 50  \w   -111.00 -76.00   0.50    0.05    --  -62.00 -48.00 174.39   70
 51  \w   -128.00-103.00   0.50    0.05    --  -79.50 -51.00 169.29   50
 52  \w   -125.00 -95.00   0.50    0.05    --  -79.50-121.00  86.13   60
 53  \w   -125.00 -99.00   0.50    0.05    --  -79.50-120.00-155.97   52
;
_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      0.0055391000
_diffrn_orient_matrix_UB_12      0.0996140000
_diffrn_orient_matrix_UB_13      -0.0155700000
_diffrn_orient_matrix_UB_21      0.0678903000
_diffrn_orient_matrix_UB_22      -0.0132356000
_diffrn_orient_matrix_UB_23      -0.0992273000
_diffrn_orient_matrix_UB_31      -0.1334556000
_diffrn_orient_matrix_UB_32      -0.0027028000
_diffrn_orient_matrix_UB_33      -0.0873336000
_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  0.0271
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            35040
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.036
_diffrn_reflns_theta_min         4.301
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    0.526
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.678
_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    1.195
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_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          0.270
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.617
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3711
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0398
_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^)+(0.0526P)^2^+0.7372P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1047
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3470
_reflns_number_total             3711
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc01500f2.cif
_cod_data_source_block           1-Dur
_cod_depositor_comments
'Adding full bibliography for 1574244--1574256.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1574246
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.871
_shelx_estimated_absorpt_t_max   0.944
_shelx_res_checksum              74582