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_1574249
_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         'C22 H21 B N2'
_chemical_formula_sum            'C22 H21 B N2'
_chemical_formula_weight         324.22
_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             2023-05-19
_audit_creation_method           'CIF-fill 1.4e (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                 110.6690(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.37660(10)
_cell_length_b                   12.64620(10)
_cell_length_c                   11.18210(10)
_cell_measurement_reflns_used    11554
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.2170
_cell_measurement_theta_min      3.4550
_cell_volume                     1769.85(3)
_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 0.999
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w     15.00  68.00   0.50    0.05    --   58.60 -98.00 -80.00  106
  2  \w    -69.00 -17.00   0.50    0.05    --  -60.16  98.00  26.00  104
  3  \w    -79.00 -26.00   0.50    0.05    --  -69.71  98.00  26.00  106
  4  \w     28.00  81.00   0.50    0.05    --   71.26 -98.00 -80.00  106
  5  \w    -85.00 -33.00   0.50    0.05    --  -76.30  98.00  26.00  104
  6  \w     33.00  86.00   0.50    0.05    --   76.61 -98.00 -80.00  106
  7  \w     41.00  93.00   0.50    0.05    --   84.39 -98.00 -80.00  104
  8  \w     38.00 109.00   0.50    0.05    --   58.60  15.00 -90.00  142
  9  \w   -110.00 -31.00   0.50    0.05    --  -60.16 -15.00  90.00  158
 10  \w   -110.00 -31.00   0.50    0.05    --  -60.16 -15.00 -30.00  158
 11  \w     29.00  79.00   0.50    0.05    --   71.26 -95.00-150.00  100
 12  \w    -92.00 -31.00   0.50    0.05    --  -76.30 112.00  30.00  122
 13  \w   -126.00 -40.00   0.50    0.05    --  -76.30 -15.00-180.00  172
 14  \w   -126.00 -40.00   0.50    0.05    --  -76.30 -15.00 -90.00  172
 15  \w     34.00  84.00   0.50    0.05    --   76.61 -95.00   0.00  100
 16  \w     34.00  84.00   0.50    0.05    --   76.61 -95.00 -30.00  100
 17  \w     42.00  92.00   0.50    0.05    --   84.39 -95.00   0.00  100
 18  \w     42.00  92.00   0.50    0.05    --   84.39 -95.00-150.00  100
 19  \w     42.00  92.00   0.50    0.05    --   84.39 -95.00  90.00  100
 20  \w     56.00 134.00   0.50    0.05    --   84.39  15.00-120.00  156
;
_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      0.0249538000
_diffrn_orient_matrix_UB_12      0.1024173000
_diffrn_orient_matrix_UB_13      -0.0587326000
_diffrn_orient_matrix_UB_21      0.1010067000
_diffrn_orient_matrix_UB_22      -0.0518491000
_diffrn_orient_matrix_UB_23      -0.0098512000
_diffrn_orient_matrix_UB_31      -0.0657167000
_diffrn_orient_matrix_UB_32      -0.0408188000
_diffrn_orient_matrix_UB_33      -0.1346642000
_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  0.0150
_diffrn_reflns_av_unetI/netI     0.0121
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17052
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.567
_diffrn_reflns_theta_min         3.531
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    0.538
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.563
_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    1.217
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_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          0.330
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3491
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0388
_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^)+(0.0504P)^2^+0.6184P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0986
_refine_ls_wR_factor_ref         0.1005
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3218
_reflns_number_total             3491
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc01500f2.cif
_cod_data_source_block           1-Mes
_cod_depositor_comments
'Adding full bibliography for 1574244--1574256.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1574249
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.843
_shelx_estimated_absorpt_t_max   0.895
_shelx_res_checksum              26484