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_1574255
_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         'C20 H14 B N3 O, C16 H36 N'
_chemical_formula_sum            'C36 H50 B N4 O'
_chemical_formula_weight         565.61
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2024-08-08
_audit_creation_method           'CIF-fill 1.5d (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                 91.8040(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.0832(2)
_cell_length_b                   10.34500(10)
_cell_length_c                   18.6658(3)
_cell_measurement_reflns_used    44829
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.4970
_cell_measurement_theta_min      2.6260
_cell_volume                     3297.09(7)
_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 2014/5 (Sheldrick, 2014)'
_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 0.975
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w     36.00  99.00   0.50    0.05    --   78.63-123.00-129.00  126
  2  \w     40.00 101.00   0.50    0.05    --   82.25-125.00-122.48  122
  3  \w     29.00  93.00   0.50    0.05    --   71.40-123.00-129.00  128
  4  \w     71.00  97.00   0.50    0.05    --   82.25-114.00 -93.84   52
  5  \w     18.00  80.00   0.50    0.05    --   58.63-123.00-129.00  124
  6  \w     37.00  92.00   0.50    0.05    --   78.63-112.00-120.00  110
  7  \w     37.00  92.00   0.50    0.05    --   78.63-112.00 -30.00  110
  8  \w     37.00  92.00   0.50    0.05    --   78.63-112.00   0.00  110
  9  \w     44.00  93.00   0.50    0.05    --   82.25-106.00  15.94   98
 10  \w     38.00  70.00   0.50    0.05    --   78.63-112.00 120.00   64
 11  \w     43.00  98.00   0.50    0.05    --   82.25-116.00 158.94  110
 12  \w     55.00  98.00   0.50    0.05    --   82.25-116.00  44.08   86
 13  \w     42.00  90.00   0.50    0.05    --   82.25-102.00-108.74   96
 14  \w     38.00 106.00   0.50    0.05    --   58.63  15.00 -90.00  136
 15  \w     45.00 126.00   0.50    0.05    --   78.63  15.00-150.00  162
 16  \w     45.00 126.00   0.50    0.05    --   78.63  15.00-150.00  162
 17  \w     46.00  98.00   0.50    0.05    --   78.63  15.00 -60.00  104
 18  \w     45.00 126.00   0.50    0.05    --   78.63  15.00  60.00  162
 19  \w     45.00 126.00   0.50    0.05    --   78.63  15.00  60.00  162
 20  \w     45.00 126.00   0.50    0.05    --   78.63  15.00 150.00  162
 21  \w     27.00  56.00   0.50    0.05    --   10.00  46.00 161.07   58
 22  \w     55.00  84.00   0.50    0.05    --   38.00  50.00   0.55   58
 23  \w     55.00  83.00   0.50    0.05    --   38.00  51.00 -38.65   56
 24  \w     20.00  46.00   0.50    0.05    --    6.00  63.00 107.65   52
 25  \w    -99.00 -35.00   0.50    0.05    --  -78.50 124.00 124.96  128
 26  \w    -91.00 -27.00   0.50    0.05    --  -69.75 123.00 -49.00  128
 27  \w    -96.00 -32.00   0.50    0.05    --  -75.18 123.00 -49.00  128
 28  \w    -99.00 -35.00   0.50    0.05    --  -78.50 121.00 -43.47  128
 29  \w    -82.00 -17.00   0.50    0.05    --  -60.27 123.00 -49.00  130
 30  \w    -99.00 -35.00   0.50    0.05    --  -78.50 121.00-115.22  128
 31  \w    -99.00 -35.00   0.50    0.05    --  -78.50 121.00-139.50  128
 32  \w    -99.00 -35.00   0.50    0.05    --  -78.50 122.00 -83.09  128
 33  \w    -99.00 -35.00   0.50    0.05    --  -78.50 121.00   1.39  128
 34  \w    -97.00 -36.00   0.50    0.05    --  -78.50 118.00  24.03  122
 35  \w    -99.00 -35.00   0.50    0.05    --  -78.50 121.00 110.79  128
 36  \w    -85.00 -38.00   0.50    0.05    --  -78.50 100.00 112.55   94
 37  \w    -89.00 -33.00   0.50    0.05    --  -75.18 112.00  30.00  112
 38  \w    -97.00 -35.00   0.50    0.05    --  -78.50 120.00  60.31  124
 39  \w    -96.00 -36.00   0.50    0.05    --  -78.50 116.00-105.45  120
 40  \w   -122.00 -43.00   0.50    0.05    --  -75.18 -15.00-120.00  158
 41  \w   -103.00 -75.00   0.50    0.05    --  -58.00 -51.00 -94.58   56
 42  \w   -121.00 -93.00   0.50    0.05    --  -78.50 -61.00 -11.77   56
 43  \w   -118.00 -90.00   0.50    0.05    --  -74.00 -54.00  41.64   56
 44  \w   -103.00 -75.00   0.50    0.05    --  -58.00 -51.00 128.10   56
 45  \w    -95.00 -67.00   0.50    0.05    --  -50.00 -50.00  91.10   56
 46  \w   -124.00 -96.00   0.50    0.05    --  -78.50 -49.00  35.18   56
 47  \w   -116.00 -86.00   0.50    0.05    --  -70.00 -45.00 149.82   60
 48  \w    -92.00 -63.00   0.50    0.05    --  -46.00 -47.00  35.88   58
 49  \w   -113.00 -82.00   0.50    0.05    --  -66.00 -44.00  78.05   62
 50  \w   -124.00 -96.00   0.50    0.05    --  -78.50 -48.00   9.33   56
 51  \w   -125.00 -94.00   0.50    0.05    --  -78.50 -42.00 175.28   62
 52  \w   -124.00 -95.00   0.50    0.05    --  -78.50 -50.00-111.39   58
 53  \w   -121.00 -90.00   0.50    0.05    --  -74.00 -43.00-139.97   62
 54  \w   -121.00 -90.00   0.50    0.05    --  -74.00 -43.00-172.24   62
 55  \w    -99.00 -71.00   0.50    0.05    --  -54.00 -50.00-136.12   56
 56  \w   -121.00 -89.00   0.50    0.05    --  -74.00 -41.00 -63.42   64
 57  \w   -126.00 -94.00   0.50    0.05    --  -78.50 -41.00 138.91   64
;
_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      0.0797730000
_diffrn_orient_matrix_UB_12      0.0693956000
_diffrn_orient_matrix_UB_13      -0.0010053000
_diffrn_orient_matrix_UB_21      -0.0000810000
_diffrn_orient_matrix_UB_22      0.0131211000
_diffrn_orient_matrix_UB_23      0.0822241000
_diffrn_orient_matrix_UB_31      0.0420943000
_diffrn_orient_matrix_UB_32      -0.1311055000
_diffrn_orient_matrix_UB_33      0.0078308000
_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  0.0444
_diffrn_reflns_av_unetI/netI     0.0124
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12050
_diffrn_reflns_point_group_measured_fraction_full 0.548
_diffrn_reflns_point_group_measured_fraction_max 0.534
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.899
_diffrn_reflns_theta_min         2.588
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    0.522
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 CrysAlisPro 1.171.43.111a (Rigaku Oxford Diffraction, 2024) Empirical 
 absorption correction using spherical harmonics, implemented in SCALE3 
 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.139
_exptl_crystal_description       block
_exptl_crystal_F_000             1228
_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          0.416
_exptl_crystal_size_mid          0.325
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     804
_refine_ls_number_reflns         12050
_refine_ls_number_restraints     176
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0433
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0707P)^2^+0.5372P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1157
_refine_ls_wR_factor_ref         0.1182
_reflns_Friedel_coverage         0.095
_reflns_Friedel_fraction_full    0.097
_reflns_Friedel_fraction_max     0.093
_reflns_number_gt                11545
_reflns_number_total             12050
_reflns_threshold_expression     'I > 2\s(I)'
_twin_dimensionality             triperiodic
_twin_formation_mechanism        gt
_twin_morphology                 polysynthetic
_twin_special_details
;
 Component 2 rotated by 179.9972\% 
 around [-0.03 0.00 1.00] (reciprocal) or [0.00 -0.00 1.00] (direct)
;
_cod_data_source_file            d5sc01500f2.cif
_cod_data_source_block           3-NCO
_cod_depositor_comments
'Adding full bibliography for 1574244--1574256.cif.'
_cod_original_sg_symbol_H-M      'P c'
_cod_database_code               1574255
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.812
_shelx_estimated_absorpt_t_max   0.945
_shelx_res_checksum              45203