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_1574256
_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 H15 B N3, C16 H36 N'
_chemical_formula_sum            'C36 H51 B N4'
_chemical_formula_weight         550.61
_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             2024-10-05
_audit_creation_method           'CIF-fill 1.5e (K.Radacki, 2005-23)'
_audit_update_record
;
2024-10-28 deposited with the CCDC.	2025-03-18 downloaded from the CCDC.
;
_cell_angle_alpha                87.7410(10)
_cell_angle_beta                 87.4770(10)
_cell_angle_gamma                78.256(2)
_cell_formula_units_Z            4
_cell_length_a                   9.5035(2)
_cell_length_b                   18.6014(4)
_cell_length_c                   19.0874(2)
_cell_measurement_reflns_used    28327
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.9980
_cell_measurement_theta_min      3.2990
_cell_volume                     3298.80(11)
_computing_cell_refinement       'CrysAlisPro 1.171.43.111a (Rigaku OD, 2024)'
_computing_data_collection
;
 CrysAlisPro system (CCD 43.128a 64-bit (release 20-06-2024))
;
_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 0.990
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w     57.00  83.00   0.50    9.95    --   38.00  44.00  75.06   52
  2  \w    -91.00 -64.00   0.50    9.95    --  -46.00 -41.00 -92.70   54
  3  \w    -95.00 -67.00   0.50    9.95    --  -50.00 -40.00-173.20   56
  4  \w    -99.00 -72.00   0.50    9.95    --  -54.00 -44.00-134.40   54
  5  \w   -100.00 -71.00   0.50    9.95    --  -54.00 -33.00  97.45   58
  6  \w   -100.00 -71.00   0.50    9.95    --  -54.00 -33.00 -51.59   58
  7  \w   -103.00 -76.00   0.50    9.95    --  -58.00 -44.00 170.67   54
  8  \w   -103.00 -76.00   0.50    9.95    --  -58.00 -42.00-105.60   54
  9  \w   -103.00 -76.00   0.50    9.95    --  -58.00 -43.00 140.02   54
 10  \w    -82.00 -21.00   0.50    9.95    --  -61.72 125.00   0.00  122
 11  \w   -107.00 -80.00   0.50    9.95    --  -62.00 -43.00  36.56   54
 12  \w   -111.00 -84.00   0.50    9.95    --  -66.00 -42.00  66.58   54
 13  \w   -115.00 -88.00   0.50    9.95    --  -70.00 -43.00  93.40   54
 14  \w   -116.00 -88.00   0.50    9.95    --  -70.00 -41.00   1.37   56
 15  \w    -92.00 -31.00   0.50    9.95    --  -71.97 125.00-180.00  122
 16  \w   -120.00 -90.00   0.50    9.95    --  -74.00 -31.00-157.62   60
 17  \w   -120.00 -90.00   0.50    9.95    --  -74.00 -31.00 -58.75   60
 18  \w    -95.00 -34.00   0.50    9.95    --  -75.12 125.00-150.00  122
 19  \w    -95.00 -34.00   0.50    9.95    --  -75.12 125.00 120.00  122
 20  \w    -95.00 -34.00   0.50    9.95    --  -75.12 125.00  30.00  122
 21  \w     36.00  97.00   0.50    9.95    --   76.61-125.00  60.00  122
 22  \w   -106.00 -36.00   0.50    9.95    --  -78.00 136.00  22.33  140
 23  \w   -120.00 -93.00   0.50    9.95    --  -78.50-121.00 137.82   54
 24  \w   -125.00 -96.00   0.50    9.95    --  -78.50 -41.00-113.64   58
 25  \w   -124.00 -80.00   0.50    9.95    --  -78.50 -20.00 -26.96   88
 26  \w   -126.00 -93.00   0.50    9.95    --  -78.50 -28.00 -78.41   66
 27  \w    -87.00 -39.00   0.50    9.95    --  -78.50 107.00 -82.81   96
 28  \w   -101.00 -37.00   0.50    9.95    --  -78.50 128.00  -3.65  128
 29  \w   -108.00 -37.00   0.50    9.95    --  -78.50 138.00  27.15  142
 30  \w   -124.00 -73.00   0.50    9.95    --  -78.50 -19.00 137.02  102
 31  \w   -123.00 -97.00   0.50    9.95    --  -78.50 -44.00  46.94   52
 32  \w   -108.00 -38.00   0.50    9.95    --  -78.50 139.00 175.21  140
 33  \w   -108.00 -37.00   0.50    9.95    --  -78.50 138.00-130.79  142
 34  \w   -126.00 -94.00   0.50    9.95    --  -78.50 -29.00  14.27   64
 35  \w   -108.00 -37.00   0.50    9.95    --  -78.50 138.00 129.73  142
 36  \w   -108.00 -37.00   0.50    9.95    --  -78.50 138.00-130.79  142
 37  \w   -107.00 -37.00   0.50    9.95    --  -78.50 137.00 -60.91  140
 38  \w   -126.00 -94.00   0.50    9.95    --  -78.50 -29.00 130.54   64
 39  \w   -101.00 -37.00   0.50    9.95    --  -78.50 128.00-137.76  128
 40  \w   -108.00 -38.00   0.50    9.95    --  -78.50 139.00 -84.40  140
 41  \w   -126.00 -95.00   0.50    9.95    --  -78.50 -31.00-174.30   62
 42  \w   -125.00 -88.00   0.50    9.95    --  -78.50 -24.00 103.13   74
 43  \w   -107.00 -37.00   0.50    9.95    --  -78.50 137.00  61.34  140
 44  \w   -126.00 -95.00   0.50    9.95    --  -78.50 -31.00  90.49   62
 45  \w   -124.00 -80.00   0.50    9.95    --  -78.50 -20.00  25.97   88
 46  \w   -103.00 -37.00   0.50    9.95    --  -78.50 131.00 175.27  132
 47  \w   -107.00 -37.00   0.50    9.95    --  -78.50 137.00 -60.91  140
 48  \w     39.00 101.00   0.50    9.95    --   80.50-126.00  48.29  124
 49  \w     40.00  96.00   0.50    9.95    --   80.50-117.00 -14.26  112
 50  \w     39.00 100.00   0.50    9.95    --   80.50-123.00-165.63  122
 51  \w     33.00  59.00   0.50    9.95    --   14.00  46.00 163.40   52
 52  \w     33.00  59.00   0.50    9.95    --   14.00  46.00 -81.58   52
 53  \w     33.00  59.00   0.50    9.95    --   14.00  46.00  72.65   52
 54  \w    -36.00 -10.00   0.50    9.95    --  -18.00 121.00  63.40   52
 55  \w     37.00  63.00   0.50    9.95    --   18.00  46.00  18.88   52
 56  \w    -71.00 -44.00   0.50    9.95    --  -26.00 -44.00  49.95   54
 57  \w    -75.00 -48.00   0.50    9.95    --  -30.00 -42.00 137.84   54
 58  \w    -79.00 -51.00   0.50    9.95    --  -34.00 -40.00 -84.99   56
 59  \w    -88.00 -59.00   0.50    9.95    --  -42.00 -39.00  -9.95   58
 60  \w   -116.00 -87.00   0.50    9.95    --  -70.00 -39.00 -94.00   58
 61  \w   -119.00 -92.00   0.50    9.95    --  -74.00 -44.00 117.84   54
 62  \w   -119.00 -91.00   0.50    9.95    --  -74.00 -40.00  -7.54   56
 63  \w   -109.00 -69.00   0.50    9.95    --  -78.50 140.00  89.43   80
 64  \w   -123.00 -97.00   0.50    9.95    --  -78.50 -44.00  79.86   52
 65  \w   -123.00 -97.00   0.50    9.95    --  -78.50 -44.00-131.20   52
 66  \w   -125.00 -94.00   0.50    9.95    --  -78.50 -30.00-105.20   62
 67  \w   -126.00 -95.00   0.50    9.95    --  -78.50 -31.00 -37.32   62
;
_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      0.0903382000
_diffrn_orient_matrix_UB_12      -0.0537135000
_diffrn_orient_matrix_UB_13      -0.0519703000
_diffrn_orient_matrix_UB_21      0.1380720000
_diffrn_orient_matrix_UB_22      0.0075412000
_diffrn_orient_matrix_UB_23      0.0359217000
_diffrn_orient_matrix_UB_31      -0.0150295000
_diffrn_orient_matrix_UB_32      -0.0649655000
_diffrn_orient_matrix_UB_33      0.0504177000
_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  0.0631
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            77310
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.350
_diffrn_reflns_theta_min         3.305
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    0.485
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.856
_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            yellow
_exptl_crystal_density_diffrn    1.109
_exptl_crystal_description       plate
_exptl_crystal_F_000             1200
_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          0.130
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     775
_refine_ls_number_reflns         12859
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0715
_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^)+(0.1189P)^2^+1.0791P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2027
_refine_ls_wR_factor_ref         0.2161
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9509
_reflns_number_total             12859
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc01500f2.cif
_cod_data_source_block           3-CN
_cod_depositor_comments
'Adding full bibliography for 1574244--1574256.cif.'
_cod_database_code               1574256
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.940
_shelx_estimated_absorpt_t_max   0.986
_shelx_res_checksum              90847