Fraternal twins: B2O2- or B2N2-doped polycyclic π systems and their formation mechanism via regiodivergent Au-versus amine catalyzed cycloadditions
Mittag, Simon M.; Klopf, Jonas; Virovets, Alexander; Peresypkina, Eugenia V.; Lerner, Hans-Wolfram; Helten, Holger; Wagner, Matthias; Dalton Transactions  (2026) –; doi:10.1039/D6DT00412A

data_7720383
_publ_section_title
;
 Fraternal twins: B<sub>2</sub>O<sub>2</sub>- or
 B<sub>2</sub>N<sub>2</sub>-doped polycyclic &#x3c0; systems and their
 formation mechanism <i>via</i> regiodivergent Au- <i>versus</i>
 amine-catalyzed cyclizations.
;
_journal_issue                   14
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              5553
_journal_page_last               5564
_journal_paper_doi               10.1039/d6dt00412a
_journal_volume                  55
_journal_year                    2026
_chemical_formula_moiety         'C25 H21 B O'
_chemical_formula_sum            'C25 H21 B O'
_chemical_formula_weight         348.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2026-01-15 deposited with the CCDC.	2026-02-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.67(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.179(6)
_cell_length_b                   15.248(2)
_cell_length_c                   10.385(2)
_cell_measurement_reflns_used    2036
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.4300
_cell_measurement_theta_min      1.6700
_cell_volume                     1906.5(11)
_computing_cell_refinement       'CrysAlisPro 1.171.43.144a (Rigaku OD, 2024)'
_computing_data_collection       'P24 beamline local software'
_computing_data_reduction        'CrysAlisPro 1.171.43.144a (Rigaku OD, 2024)'
_computing_publication_material  'IUCr PublCIF online service'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT (G. M. Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector
'X-Spectrum Lambda 7.5M CdTe photon-counting detector'
_diffrn_detector_area_resol_mean 18.2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device
'DESY Petra3 P24 beamline, Huber diffractometer, Lambda 7.5M CdTe'
_diffrn_measurement_method       '\f scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.560
_diffrn_reflns_av_R_equivalents  0.0599
_diffrn_reflns_av_sigmaI/netI    0.0174
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17112
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        19.633
_diffrn_reflns_theta_max         26.847
_diffrn_reflns_theta_min         1.698
_diffrn_source                   synchrotron
_exptl_absorpt_coefficient_mu    0.047
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87263
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.144a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       0.113(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         17112
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.183
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0587
_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^)+(0.1440P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2000
_refine_ls_wR_factor_ref         0.2066
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13729
_reflns_number_total             17112
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by 5.1811\% 
around [0.04 -0.85 -0.53] (reciprocal) or [-0.05 -0.59 -0.80] (direct)
;
_cod_data_source_file            d6dt00412a2.cif
_cod_data_source_block           BO_SM346-1_P24
_cod_depositor_comments
'Adding full bibliography for 7720366--7720383.cif.'
_cod_original_cell_volume        1906.4(10)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7720383
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.991
_shelx_estimated_absorpt_t_max   0.993
_cell_oxdiff_measurement_reflns_used 43946
_oxdiff_exptl_absorpt_empirical_full_min 0.874
_oxdiff_exptl_absorpt_empirical_full_max 1.243
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_twin_items               2
_oxdiff_twin_integration_method  simultaneous
_shelx_res_checksum              41608