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_7161048
_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_absolute_configuration unk
_chemical_formula_moiety         'C33 H33 B N2 O2'
_chemical_formula_sum            'C33 H33 B N2 O2'
_chemical_formula_weight         500.42
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7084(3)
_cell_length_b                   32.0567(13)
_cell_length_c                   10.0958(3)
_cell_measurement_reflns_used    1931
_cell_measurement_temperature    302.9(9)
_cell_measurement_theta_max      71.8870
_cell_measurement_theta_min      4.6080
_cell_volume                     2818.37(17)
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      302.9(9)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3385
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.979
_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    -82.00 -55.00   1.00   31.80    --  -43.18 125.00  30.00   27
  2  \w   -108.00 -19.00   1.00   31.80    --  -43.18 -38.00 120.00   89
  3  \w     32.00  81.00   1.00   31.80    --   43.18 -99.00 -30.00   49
  4  \w     75.00 112.00   1.00  127.18    --  104.94-125.00 -30.00   37
  5  \w     43.00  97.00   1.00  127.18    --  104.94 -95.00 -30.00   54
  6  \w     32.00  73.00   1.00  127.18    --  104.94-125.00 -30.00   41
  7  \w     23.00 154.00   1.00  127.18    --  104.94   0.00 -60.00  131
;
_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      0.0329107000
_diffrn_orient_matrix_UB_12      -0.0194603000
_diffrn_orient_matrix_UB_13      0.1366079000
_diffrn_orient_matrix_UB_21      0.0430393000
_diffrn_orient_matrix_UB_22      0.0433683000
_diffrn_orient_matrix_UB_23      0.0545182000
_diffrn_orient_matrix_UB_31      -0.1683535000
_diffrn_orient_matrix_UB_32      0.0071518000
_diffrn_orient_matrix_UB_33      0.0406708000
_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  0.0334
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            14530
_diffrn_reflns_point_group_measured_fraction_full 0.667
_diffrn_reflns_point_group_measured_fraction_max 0.645
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.976
_diffrn_reflns_theta_min         4.592
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.565
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.777
_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    1.179
_exptl_crystal_description       needle
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.479
_exptl_crystal_size_mid          0.079
_exptl_crystal_size_min          0.053
_refine_diff_density_max         0.126
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.0(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     350
_refine_ls_number_reflns         3634
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0519
_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^)+(0.0554P)^2^+0.8714P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1226
_refine_ls_wR_factor_ref         0.1345
_reflns_Friedel_coverage         0.245
_reflns_Friedel_fraction_full    0.291
_reflns_Friedel_fraction_max     0.270
_reflns_number_gt                3098
_reflns_number_total             3634
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01979f3.cif
_cod_data_source_block           jsc20071
_cod_depositor_comments
'Adding full bibliography for 7161044--7161048.cif.'
_cod_original_sg_symbol_Hall     ' P 2c -2n'
_cod_database_code               7161048
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C33 H33 B N2 O2'
_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:
 C00C(H00C), C00E(H00E), C00G(H00G), C00I(H00I), C00K(H00K), C00L(H00L),
 C00N(H00N), C00O(H00O), C00P(H00P), C00S(H00S), C00W(H00W), C00Y(H00Y)
2.b Idealised Me refined as rotating group:
 C00Q(H00A,H00B,H00D), C00R(H00F,H00H,H00J), C00V(H00M,H00Q,H00R), C00X(H00T,
 H00U,H00V), C010(H01A,H01B,H01C), C011(H01D,H01E,H01F), C012(H01G,H01H,H01I)
;
_shelx_res_checksum              48631
_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 1.623
_oxdiff_exptl_absorpt_empirical_full_min 0.508