Dynamic N→B coordination and anion-selective turn-on fluorescence in oxadiazole-functionalized organoboranes.
Schepper, Jonas D. W.; Orthaber, Andreas; Pammer, Frank; Organic & biomolecular chemistry 24 (2026) 2683–2695; doi:10.1039/d5ob01979f

data_7161047
_publ_section_title
;
 Dynamic N&#x2192;B coordination and anion-selective turn-on fluorescence
 in oxadiazole-functionalized organoboranes.
;
_journal_issue                   13
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2683
_journal_page_last               2695
_journal_paper_doi               10.1039/d5ob01979f
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         'C33 H33 B N2 O'
_chemical_formula_sum            'C33 H33 B N2 O'
_chemical_formula_weight         484.42
_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
_audit_creation_date             2025-11-29
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2025-12-08 deposited with the CCDC.	2026-02-24 downloaded from the CCDC.
;
_cell_angle_alpha                99.257(5)
_cell_angle_beta                 101.748(5)
_cell_angle_gamma                108.129(5)
_cell_formula_units_Z            2
_cell_length_a                   9.7571(5)
_cell_length_b                   11.1700(7)
_cell_length_c                   14.0701(9)
_cell_measurement_reflns_used    3508
_cell_measurement_temperature    301.9(6)
_cell_measurement_theta_max      72.4620
_cell_measurement_theta_min      4.2660
_cell_volume                     1384.76(16)
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      301.9(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3385
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -66.00  -6.00   1.00    1.00    --  -43.06 125.00  90.00   60
  2  \w    -40.00 -14.00   1.00    1.00    --  -43.06  38.00  30.00   26
  3  \w    -31.00  -6.00   1.00    1.00    --  -43.06 125.00 150.00   25
  4  \w    -63.00  29.00   1.00    1.00    --  -43.06  38.00  60.00   92
  5  \w   -110.00 -19.00   1.00    1.00    --  -43.06 -38.00-120.00   91
  6  \w     60.00  97.00   1.00    1.00    --   43.06-125.00-180.00   37
  7  \w     40.00  66.00   1.00    3.71    --  104.94 -77.00 120.00   26
  8  \w     34.00 112.00   1.00    3.71    --  104.94-125.00-150.00   78
  9  \w     65.00 112.00   1.00    3.71    --  104.94-125.00 -30.00   47
 10  \w     34.00 123.00   1.00    3.71    --  104.94 -45.00-180.00   89
 11  \w     45.00  80.00   1.00    3.71    --  104.94-112.00  81.00   35
 12  \w    108.00 159.00   1.00    3.71    --  104.94 125.00 120.00   51
 13  \w    102.00 177.00   1.00    3.71    --  104.94 125.00-150.00   75
 14  \w     78.00 168.00   1.00    3.71    --  104.94  30.00  60.00   90
 15  \w     79.00 106.00   1.00    3.71    --  104.94 -95.00 -60.00   27
 16  \w    105.00 130.00   1.00    3.71    --  104.94 112.00 174.00   25
 17  \w     98.00 126.00   1.00    3.71    --  104.94 -77.00 120.00   28
 18  \w    103.00 165.00   1.00    3.71    --  104.94  77.00 -90.00   62
 19  \w    137.00 162.00   1.00    3.71    --  104.94  77.00-150.00   25
 20  \w     84.00 109.00   1.00    3.71    --  104.94-112.00  81.00   25
 21  \w     81.00 106.00   1.00    3.71    --  104.94 -95.00 -30.00   25
 22  \w     77.00 176.00   1.00    3.71    --  104.94  61.00 -30.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0168468000
_diffrn_orient_matrix_UB_12      0.0913462000
_diffrn_orient_matrix_UB_13      -0.0691491000
_diffrn_orient_matrix_UB_21      0.0851634000
_diffrn_orient_matrix_UB_22      0.1183063000
_diffrn_orient_matrix_UB_23      0.0893218000
_diffrn_orient_matrix_UB_31      0.1491419000
_diffrn_orient_matrix_UB_32      0.0043400000
_diffrn_orient_matrix_UB_33      -0.0227597000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20186
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.024
_diffrn_reflns_theta_min         4.291
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.531
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.652
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
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_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_description       block
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.232
_exptl_crystal_size_mid          0.232
_exptl_crystal_size_min          0.225
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         5343
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0514
_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^)+(0.0635P)^2^+0.3074P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1310
_refine_ls_wR_factor_ref         0.1453
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4254
_reflns_number_total             5343
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01979f3.cif
_cod_data_source_block           jsc20067
_cod_depositor_comments
'Adding full bibliography for 7161044--7161048.cif.'
_cod_original_cell_volume        1384.75(15)
_cod_database_code               7161047
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C33 H33 B N2 O'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C12(H12), C16(H16), C19(H19), C21(H21), C23(H23), C24(H24), C26(H26),
 C27(H27), C30(H30), C31(H31), C34(H34)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C25(H25A,H25B,H25C), C28(H28A,H28B,H28C), C33(H33A,H33B,
 H33C), C35(H35A,H35B,H35C), C36(H36A,H36B,H36C), C37(H37A,H37B,H37C)
;
_shelx_res_checksum              64643
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.716
_oxdiff_exptl_absorpt_empirical_full_min 0.436