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_7720366
_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         'C12 H7 Br'
_chemical_formula_sum            'C12 H7 Br'
_chemical_formula_weight         231.09
_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
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.83154(13)
_cell_length_b                   10.50963(8)
_cell_length_c                   7.48872(6)
_cell_measurement_reflns_used    22892
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.6880
_cell_measurement_theta_min      2.6310
_cell_volume                     931.186(15)
_computing_cell_refinement       'CrysAlisPro 1.171.42.43a (Rigaku OD, 2022)'
_computing_data_collection       'P24 beamline local software'
_computing_data_reduction        'CrysAlisPro 1.171.42.43a (Rigaku OD, 2022)'
_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      150(2)
_diffrn_detector
'X-Spectrum Lambda 7.5M CdTe photon-counting detector'
_diffrn_detector_area_resol_mean 18.2
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.924
_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     0.500
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_unetI/netI     0.0566
_diffrn_reflns_Laue_measured_fraction_full 0.954
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            26495
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.896
_diffrn_reflns_theta_full        17.458
_diffrn_reflns_theta_max         24.620
_diffrn_reflns_theta_min         2.643
_diffrn_source                   synchrotron
_exptl_absorpt_coefficient_mu    1.717
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60651
_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    1.648
_exptl_crystal_description       prism
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.214(19)
_refine_ls_extinction_coef       0.037(5)
_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   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         4051
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0337
_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^)+(0.0268P)^2^+0.1244P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0898
_refine_ls_wR_factor_ref         0.0908
_reflns_Friedel_coverage         0.826
_reflns_Friedel_fraction_full    0.974
_reflns_Friedel_fraction_max     0.864
_reflns_number_gt                3880
_reflns_number_total             4051
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6dt00412a2.cif
_cod_data_source_block           S2_sm325-1_P24
_cod_depositor_comments
'Adding full bibliography for 7720366--7720383.cif.'
_cod_database_code               7720366
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.747
_shelx_estimated_absorpt_t_max   0.934
_shelx_res_checksum              73426