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_1574245
_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_absolute_configuration unk
_chemical_formula_moiety         'C33 H40 B Li N2 O2'
_chemical_formula_sum            'C33 H40 B Li N2 O2'
_chemical_formula_weight         514.42
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2024-09-20
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2851(2)
_cell_length_b                   15.5100(2)
_cell_length_c                   17.2399(2)
_cell_measurement_reflns_used    13024
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.3010
_cell_measurement_theta_min      4.6610
_cell_volume                     3017.53(7)
_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 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w     38.00 103.00   0.50    0.17    --   85.25-131.00-146.26  130
  2  \w     39.00 107.00   0.50    0.17    --   85.25-137.00 -76.05  136
  3  \w     41.00  66.00   0.50    0.17    --   85.25-106.00 -57.56   50
  4  \w     60.00  91.00   0.50    0.17    --   85.25 -95.00 -36.61   62
  5  \w     14.00  70.00   0.50    0.05    --   58.60-101.00  47.00  112
  6  \w     27.00  83.00   0.50    0.05    --   71.26-101.00  47.00  112
  7  \w     44.00  69.00   0.50    0.17    --   85.25 -95.00  57.00   50
  8  \w     38.00  92.00   0.50    0.17    --   82.35-101.00  47.00  108
  9  \w     43.00  89.00   0.50    0.17    --   85.25 -98.00  75.18   92
 10  \w     44.00  70.00   0.50    0.17    --   85.25 -73.00-110.28   52
 11  \w     17.00  43.00   0.50    0.05    --    6.00  64.00 130.22   52
 12  \w     30.00  60.00   0.50    0.05    --   18.00  57.00 -25.52   60
 13  \w    107.00 133.00   0.50    0.17    --   85.25  49.00 122.15   52
 14  \w     97.00 136.00   0.50    0.17    --   85.25  40.00 118.37   78
 15  \w     97.00 132.00   0.50    0.17    --   85.25  58.00  36.47   70
 16  \w     97.00 132.00   0.50    0.17    --   85.25  59.00-156.87   70
 17  \w     95.00 120.00   0.50    0.17    --   85.25 128.00 -62.24   50
 18  \w    100.00 131.00   0.50    0.17    --   85.25 119.00-140.01   62
 19  \w    102.00 128.00   0.50    0.17    --   85.25 117.00 -32.52   52
 20  \w     97.00 132.00   0.50    0.17    --   85.25 125.00 139.08   70
 21  \w      4.00  30.00   0.50    0.05    --   -6.00  69.00  13.00   52
 22  \w     -6.00  20.00   0.50    0.05    --  -10.00  78.00 117.66   52
 23  \w    -72.00 -16.00   0.50    0.05    --  -60.30 101.00 151.00  112
 24  \w    -81.00 -26.00   0.50    0.05    --  -69.94 101.00 151.00  110
 25  \w    -88.00 -32.00   0.50    0.17    --  -76.30 101.00 151.00  112
 26  \w   -124.00 -94.00   0.50    0.17    --  -79.50 -64.00 -65.28   60
 27  \w   -127.00 -92.00   0.50    0.17    --  -79.50 -54.00 -32.10   70
 28  \w   -128.00 -93.00   0.50    0.17    --  -79.50 -49.00  -8.10   70
 29  \w   -124.00 -92.00   0.50    0.17    --  -79.50 -63.00  80.70   64
 30  \w   -123.00 -88.00   0.50    0.17    --  -74.00 -50.00 132.33   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      0.1007011000
_diffrn_orient_matrix_UB_12      -0.0157382000
_diffrn_orient_matrix_UB_13      0.0589290000
_diffrn_orient_matrix_UB_21      -0.0126302000
_diffrn_orient_matrix_UB_22      0.0930357000
_diffrn_orient_matrix_UB_23      0.0297657000
_diffrn_orient_matrix_UB_31      -0.0913027000
_diffrn_orient_matrix_UB_32      -0.0303771000
_diffrn_orient_matrix_UB_33      0.0606398000
_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  0.0308
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            29040
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.332
_diffrn_reflns_theta_min         3.834
_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  0.825
_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 pale yellow'
_exptl_crystal_density_diffrn    1.132
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_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          0.170
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.115
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.534
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Refined as an inversion twin.'
_refine_ls_abs_structure_Flack   0.3(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     445
_refine_ls_number_reflns         6015
_refine_ls_number_restraints     480
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0615
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0955P)^2^+1.3489P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1653
_refine_ls_wR_factor_ref         0.1703
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_full    0.971
_reflns_Friedel_fraction_max     0.921
_reflns_number_gt                5432
_reflns_number_total             6015
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc01500f2.cif
_cod_data_source_block           2-Li
_cod_depositor_comments
'Adding full bibliography for 1574244--1574256.cif.'
_cod_database_code               1574245
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.915
_shelx_estimated_absorpt_t_max   0.942
_shelx_res_checksum              32159