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_1574252
_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         'C14 H13 B N2'
_chemical_formula_sum            'C14 H13 B N2'
_chemical_formula_weight         220.07
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2024-04-16
_audit_creation_method           'CIF-fill 1.4u (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            8
_cell_length_a                   23.6005(2)
_cell_length_b                   6.89970(10)
_cell_length_c                   14.16730(10)
_cell_measurement_reflns_used    30291
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.2620
_cell_measurement_theta_min      3.6090
_cell_volume                     2306.95(4)
_computing_cell_refinement       'CrysAlisPro 1.171.43.111a (Rigaku OD, 2024)'
_computing_data_collection
;
 CrysAlisPro system (CCD 43.112a 64-bit (release 01-03-2024))
;
_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 1.000
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w    -36.00 -10.00   0.50    0.23    --  -14.00 121.00-161.97   52
  2  \w    -87.00 -16.00   0.50    0.23    --  -61.61 127.00 -94.00  142
  3  \w   -101.00 -31.00   0.50    0.23    --  -76.35 127.00 -94.00  140
  4  \w    -97.00 -35.00   0.50    0.23    --  -79.50 116.00 -51.48  124
  5  \w    -97.00 -26.00   0.50    0.23    --  -71.68 127.00 -94.00  142
  6  \w    -97.00 -36.00   0.50    0.23    --  -79.50 114.00-150.47  122
  7  \w    -97.00 -36.00   0.50    0.23    --  -79.50 114.00-109.83  122
  8  \w    -97.00 -36.00   0.50    0.23    --  -79.50 115.00 -12.34  122
  9  \w    -97.00 -36.00   0.50    0.23    --  -79.50 114.00  23.67  122
 10  \w    -85.00 -17.00   0.50    0.23    --  -61.61 125.00  30.00  136
 11  \w    -97.00 -36.00   0.50    0.23    --  -79.50 114.00  55.79  122
 12  \w    -97.00 -36.00   0.50    0.23    --  -79.50 115.00 136.25  122
 13  \w    -92.00 -33.00   0.50    0.23    --  -76.35 112.00  60.00  118
 14  \w    -97.00 -36.00   0.50    0.23    --  -79.50 114.00  55.79  122
 15  \w    -92.00 -33.00   0.50    0.23    --  -76.35 112.00-150.00  118
 16  \w     28.00  56.00   0.50    0.23    --   14.00  60.00-120.71   56
 17  \w     33.00  60.00   0.50    0.23    --   18.00  56.00-167.31   54
 18  \w     58.00  89.00   0.50    0.23    --   42.00  51.00-147.25   62
 19  \w     32.00  60.00   0.50    0.23    --   18.00  58.00 -70.84   56
 20  \w     38.00  69.00   0.50    0.23    --   22.00  51.00  -7.49   62
 21  \w     28.00  56.00   0.50    0.23    --   14.00  60.00  39.51   56
 22  \w     32.00  60.00   0.50    0.23    --   18.00  59.00  78.85   56
 23  \w     54.00  85.00   0.50    0.23    --   38.00  49.00  32.36   62
 24  \w     54.00 128.00   0.50    0.23    --   80.28  15.00 120.00  148
 25  \w     54.00 128.00   0.50    0.23    --   80.28  15.00-180.00  148
 26  \w     54.00 128.00   0.50    0.23    --   80.28  15.00-180.00  148
 27  \w     21.00  86.00   0.50    0.23    --   60.16-127.00-169.00  130
 28  \w     28.00  99.00   0.50    0.23    --   73.63-127.00-169.00  142
 29  \w     28.00  99.00   0.50    0.23    --   73.63-127.00-169.00  142
 30  \w     35.00 101.00   0.50    0.23    --   80.28-127.00-169.00  132
 31  \w     40.00  86.00   0.50    0.23    --   80.28 -95.00-150.00   92
 32  \w     42.00  91.00   0.50    0.23    --   83.50 -99.00-103.23   98
 33  \w     19.00  66.00   0.50    0.23    --   60.16 -95.00   0.00   94
 34  \w     33.00  79.00   0.50    0.23    --   73.63 -95.00  30.00   92
 35  \w     40.00  86.00   0.50    0.23    --   80.28 -95.00  30.00   92
 36  \w     40.00  86.00   0.50    0.23    --   80.28 -95.00 120.00   92
 37  \w    -54.00 -28.00   0.50    0.23    --  -14.00 -57.00  80.97   52
 38  \w    -96.00 -65.00   0.50    0.23    --  -50.00 -52.00 121.80   62
 39  \w    -90.00 -57.00   0.50    0.23    --  -42.00 -44.00  33.07   66
 40  \w    -96.00 -65.00   0.50    0.23    --  -50.00 -52.00-114.29   62
 41  \w    -97.00 -66.00   0.50    0.23    --  -50.00 -48.00-152.79   62
 42  \w   -124.00 -56.00   0.50    0.23    --  -76.35 -15.00 -90.00  136
 43  \w   -125.00 -94.00   0.50    0.23    --  -79.50 -55.00 -76.60   62
 44  \w   -125.00 -95.00   0.50    0.23    --  -79.50 -54.00-146.43   60
 45  \w   -104.00 -73.00   0.50    0.23    --  -58.00 -52.00 -93.51   62
 46  \w   -122.00 -94.00   0.50    0.23    --  -79.50 -64.00 -32.32   56
 47  \w   -104.00 -74.00   0.50    0.23    --  -58.00 -51.00 -42.34   60
 48  \w   -126.00 -95.00   0.50    0.23    --  -79.50 -52.00  21.02   62
 49  \w   -126.00 -96.00   0.50    0.23    --  -79.50 -49.00-105.77   60
 50  \w   -104.00 -73.00   0.50    0.23    --  -58.00 -52.00  53.63   62
 51  \w   -119.00 -89.00   0.50    0.23    --  -74.00 -56.00  65.40   60
 52  \w   -109.00 -78.00   0.50    0.23    --  -62.00 -47.00  95.82   62
 53  \w   -126.00 -96.00   0.50    0.23    --  -79.50 -49.00 107.23   60
 54  \w   -126.00 -96.00   0.50    0.23    --  -79.50 -49.00 148.09   60
 55  \w   -109.00 -78.00   0.50    0.23    --  -62.00 -49.00 179.93   62
 56  \w   -114.00 -81.00   0.50    0.23    --  -66.00 -45.00 148.40   66
 57  \w   -105.00 -74.00   0.50    0.23    --  -58.00 -47.00  16.54   62
 58  \w   -123.00 -87.00   0.50    0.23    --  -74.00 -35.00 -10.16   72
 59  \w   -123.00 -87.00   0.50    0.23    --  -74.00 -35.00-157.38   72
 60  \w   -128.00 -94.00   0.50    0.23    --  -79.50 -42.00-126.29   68
 61  \w   -127.00 -92.00   0.50    0.23    --  -78.00 -37.00-172.31   70
 62  \w   -110.00 -78.00   0.50    0.23    --  -62.00 -46.00 -61.60   64
 63  \w   -128.00 -65.00   0.50    0.23    --  -79.50 -17.00 -46.16  126
 64  \w   -125.00 -90.00   0.50    0.23    --  -79.50-126.00  58.19   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      -0.1155792000
_diffrn_orient_matrix_UB_12      -0.0437749000
_diffrn_orient_matrix_UB_13      -0.0578060000
_diffrn_orient_matrix_UB_21      0.1169283000
_diffrn_orient_matrix_UB_22      -0.0482676000
_diffrn_orient_matrix_UB_23      0.0460680000
_diffrn_orient_matrix_UB_31      -0.1510799000
_diffrn_orient_matrix_UB_32      -0.0038382000
_diffrn_orient_matrix_UB_33      0.0797575000
_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  0.0645
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            51948
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.696
_diffrn_reflns_theta_min         3.746
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    0.574
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.412
_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    1.267
_exptl_crystal_description       plate
_exptl_crystal_F_000             928
_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          0.690
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Refined as an inversion twin.'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4549
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0336
_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^)+(0.0562P)^2^+0.3275P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0908
_reflns_Friedel_coverage         0.874
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.936
_reflns_number_gt                4406
_reflns_number_total             4549
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc01500f2.cif
_cod_data_source_block           1-Me
_cod_depositor_comments
'Adding full bibliography for 1574244--1574256.cif.'
_cod_database_code               1574252
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.693
_shelx_estimated_absorpt_t_max   0.977
_shelx_res_checksum              43684