#------------------------------------------------------------------------------
#$Date: 2026-02-28 02:28:36 +0100 (Sat 28 de Feb de 2026) $
#$Revision: 304661 $
#$URL: svn://www.crystallography.net/cod/cif/7/72/03/7720367.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7720367
loop_
_publ_author_name
'Mittag, Simon M.'
'Klopf, Jonas'
'Virovets, Alexander'
'Peresypkina, Eugenia V.'
'Lerner, Hans-Wolfram'
'Helten, Holger'
'Wagner, Matthias'
_publ_section_title
;
 Fraternal twins: B2O2- or B2N2-doped polycyclic π systems and their
 formation mechanism via regiodivergent Au-versus amine catalyzed
 cycloadditions
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D6DT00412A
_journal_year                    2026
_chemical_formula_moiety         'C23 H25 B O'
_chemical_formula_sum            'C23 H25 B O'
_chemical_formula_weight         328.24
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.9307(15)
_cell_length_b                   9.9600(7)
_cell_length_c                   25.546(2)
_cell_measurement_reflns_used    1043
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      22.4750
_cell_measurement_theta_min      3.0530
_cell_volume                     4053.4(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.43a (Rigaku OD, 2022)'
_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_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      173(2)
_diffrn_detector                 'image plate'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            'STOE image plate (34 cm diameter)'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0669
_diffrn_reflns_av_unetI/netI     0.0785
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9500
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.681
_diffrn_reflns_theta_min         2.540
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_exptl_absorpt_coefficient_mu    0.063
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92786
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.43a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.076
_exptl_crystal_description       'elongated prism'
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3825
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.1197
_refine_ls_R_factor_gt           0.0549
_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/[σ²(Fo²)+(0.0591P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1205
_refine_ls_wR_factor_ref         0.1476
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2100
_reflns_number_total             3825
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d6dt00412a2.cif
_cod_data_source_block           B1SI_wa3662_sm313
_cod_database_code               7720367
_shelx_shelxl_version_number     2019/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.975
_shelx_estimated_absorpt_t_max   0.992
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.4305(2) 0.4888(3) 0.70118(12) 0.0481(7) Uani 1 1 d . . . . .
O1A O 0.4278(8) 0.6252(12) 0.7093(4) 0.070(3) Uani 0.6 1 d . . P A 1
H1A H 0.428759 0.664985 0.680275 0.105 Uiso 0.6 1 calc R U P A 1
O1B O 0.4011(11) 0.6174(16) 0.6932(5) 0.067(4) Uani 0.4 1 d . . P A 2
H1B H 0.380061 0.623077 0.663101 0.101 Uiso 0.4 1 calc R U P A 2
C1 C 0.45566(15) 0.5937(2) 0.58911(9) 0.0424(6) Uani 1 1 d . . . . .
C2 C 0.42617(15) 0.6993(2) 0.57487(9) 0.0431(6) Uani 1 1 d . . . . .
C3 C 0.39360(15) 0.8213(2) 0.55928(9) 0.0428(6) Uani 1 1 d . . . . .
C4 C 0.36647(14) 0.9276(2) 0.54561(9) 0.0413(6) Uani 1 1 d . . . . .
C5 C 0.33293(15) 1.0586(2) 0.52879(9) 0.0457(6) Uani 1 1 d . . . . .
C6 C 0.24735(19) 1.0375(3) 0.50377(12) 0.0709(9) Uani 1 1 d . . . . .
H6A H 0.253004 0.977873 0.473471 0.106 Uiso 1 1 calc R U . . .
H6B H 0.224729 1.124238 0.492365 0.106 Uiso 1 1 calc R U . . .
H6C H 0.209161 0.996951 0.529342 0.106 Uiso 1 1 calc R U . . .
C7 C 0.3235(2) 1.1492(3) 0.57730(11) 0.0724(9) Uani 1 1 d . . . . .
H7A H 0.286114 1.105875 0.602675 0.109 Uiso 1 1 calc R U . . .
H7B H 0.299601 1.235811 0.566797 0.109 Uiso 1 1 calc R U . . .
H7C H 0.378645 1.163617 0.593299 0.109 Uiso 1 1 calc R U . . .
C8 C 0.3940(2) 1.1216(3) 0.49028(14) 0.0890(11) Uani 1 1 d . . . . .
H8A H 0.450196 1.124584 0.505908 0.134 Uiso 1 1 calc R U . . .
H8B H 0.375675 1.213061 0.481933 0.134 Uiso 1 1 calc R U . . .
H8C H 0.395681 1.067891 0.458157 0.134 Uiso 1 1 calc R U . . .
C11 C 0.48305(14) 0.4196(2) 0.65631(9) 0.0393(6) Uani 1 1 d . . . . .
C12 C 0.49351(14) 0.4698(2) 0.60492(9) 0.0374(5) Uani 1 1 d . . . . .
C13 C 0.54097(16) 0.3990(2) 0.56813(9) 0.0458(6) Uani 1 1 d . . . . .
H13 H 0.546624 0.433060 0.533572 0.055 Uiso 1 1 calc R U . . .
C14 C 0.57972(16) 0.2799(2) 0.58167(10) 0.0518(7) Uani 1 1 d . . . . .
H14 H 0.612400 0.232870 0.556544 0.062 Uiso 1 1 calc R U . . .
C15 C 0.57102(16) 0.2293(2) 0.63151(10) 0.0505(7) Uani 1 1 d . . . . .
H15 H 0.597970 0.147791 0.641002 0.061 Uiso 1 1 calc R U . . .
C16 C 0.52271(16) 0.2981(2) 0.66773(9) 0.0465(6) Uani 1 1 d . . . . .
H16 H 0.516287 0.261020 0.701763 0.056 Uiso 1 1 calc R U . . .
C21 C 0.39254(15) 0.4025(2) 0.74630(9) 0.0415(6) Uani 1 1 d . . . . .
C22 C 0.43603(17) 0.3798(3) 0.79323(10) 0.0526(7) Uani 1 1 d . . . . .
C23 C 0.4013(2) 0.2930(3) 0.83031(11) 0.0721(9) Uani 1 1 d . . . . .
H23 H 0.430329 0.279439 0.862356 0.087 Uiso 1 1 calc R U . . .
C24 C 0.3274(2) 0.2271(3) 0.82239(12) 0.0772(10) Uani 1 1 d . . . . .
C25 C 0.28403(18) 0.2510(3) 0.77664(12) 0.0659(8) Uani 1 1 d . . . . .
H25 H 0.231981 0.206971 0.770786 0.079 Uiso 1 1 calc R U . . .
C26 C 0.31507(16) 0.3384(2) 0.73898(9) 0.0475(6) Uani 1 1 d . . . . .
C27 C 0.5211(2) 0.4431(3) 0.80203(12) 0.0754(9) Uani 1 1 d . . . . .
H27A H 0.564328 0.388685 0.784880 0.113 Uiso 1 1 calc R U . . .
H27B H 0.532570 0.447734 0.839672 0.113 Uiso 1 1 calc R U . . .
H27C H 0.521470 0.533877 0.787246 0.113 Uiso 1 1 calc R U . . .
C28 C 0.2945(2) 0.1288(5) 0.86311(17) 0.141(2) Uani 1 1 d . . . . .
H28A H 0.263834 0.178098 0.890255 0.211 Uiso 1 1 calc R U . . .
H28B H 0.341719 0.080777 0.879044 0.211 Uiso 1 1 calc R U . . .
H28C H 0.256741 0.064276 0.846260 0.211 Uiso 1 1 calc R U . . .
C29 C 0.26394(18) 0.3653(3) 0.69015(10) 0.0668(8) Uani 1 1 d . . . . .
H29A H 0.235642 0.452255 0.693430 0.100 Uiso 1 1 calc R U . . .
H29B H 0.221934 0.294291 0.685797 0.100 Uiso 1 1 calc R U . . .
H29C H 0.301148 0.366748 0.659602 0.100 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1A B1 C21 114.9(5) . . ?
O1B B1 C21 119.3(8) . . ?
O1A B1 C11 123.8(6) . . ?
O1B B1 C11 118.6(7) . . ?
C21 B1 C11 120.14(19) . . ?
B1 O1A H1A 109.5 . . ?
B1 O1B H1B 109.5 . . ?
C2 C1 C12 177.8(3) . . ?
C1 C2 C3 178.8(3) . . ?
C4 C3 C2 179.1(3) . . ?
C3 C4 C5 179.9(3) . . ?
C4 C5 C8 108.8(2) . . ?
C4 C5 C6 109.0(2) . . ?
C8 C5 C6 111.1(2) . . ?
C4 C5 C7 108.6(2) . . ?
C8 C5 C7 110.0(2) . . ?
C6 C5 C7 109.3(2) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C16 C11 C12 116.5(2) . . ?
C16 C11 B1 117.8(2) . . ?
C12 C11 B1 125.62(19) . . ?
C13 C12 C11 120.64(19) . . ?
C13 C12 C1 118.2(2) . . ?
C11 C12 C1 121.1(2) . . ?
C14 C13 C12 120.5(2) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 120.1(2) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 119.5(2) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C15 C16 C11 122.7(2) . . ?
C15 C16 H16 118.6 . . ?
C11 C16 H16 118.6 . . ?
C26 C21 C22 118.4(2) . . ?
C26 C21 B1 119.6(2) . . ?
C22 C21 B1 121.9(2) . . ?
C23 C22 C21 118.9(3) . . ?
C23 C22 C27 120.8(3) . . ?
C21 C22 C27 120.2(3) . . ?
C24 C23 C22 122.7(3) . . ?
C24 C23 H23 118.7 . . ?
C22 C23 H23 118.7 . . ?
C23 C24 C25 118.4(3) . . ?
C23 C24 C28 120.4(3) . . ?
C25 C24 C28 121.2(4) . . ?
C24 C25 C26 121.1(3) . . ?
C24 C25 H25 119.4 . . ?
C26 C25 H25 119.4 . . ?
C25 C26 C21 120.4(2) . . ?
C25 C26 C29 119.4(3) . . ?
C21 C26 C29 120.2(2) . . ?
C22 C27 H27A 109.5 . . ?
C22 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C22 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C24 C28 H28A 109.5 . . ?
C24 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C24 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C26 C29 H29A 109.5 . . ?
C26 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C26 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 O1A 1.375(12) . ?
B1 O1B 1.380(16) . ?
B1 C21 1.560(4) . ?
B1 C11 1.578(4) . ?
O1A H1A 0.8400 . ?
O1B H1B 0.8400 . ?
C1 C2 1.208(3) . ?
C1 C12 1.432(3) . ?
C2 C3 1.380(3) . ?
C3 C4 1.196(3) . ?
C4 C5 1.474(3) . ?
C5 C8 1.520(4) . ?
C5 C6 1.520(4) . ?
C5 C7 1.541(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C11 C16 1.396(3) . ?
C11 C12 1.415(3) . ?
C12 C13 1.397(3) . ?
C13 C14 1.381(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.376(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C26 1.402(3) . ?
C21 C22 1.403(3) . ?
C22 C23 1.397(4) . ?
C22 C27 1.511(4) . ?
C23 C24 1.362(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.379(4) . ?
C24 C28 1.522(4) . ?
C25 C26 1.388(3) . ?
C25 H25 0.9500 . ?
C26 C29 1.514(4) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1A B1 C11 C16 142.1(5) . . . . ?
O1B B1 C11 C16 170.8(8) . . . . ?
C21 B1 C11 C16 -25.4(4) . . . . ?
O1A B1 C11 C12 -38.2(6) . . . . ?
O1B B1 C11 C12 -9.5(8) . . . . ?
C21 B1 C11 C12 154.4(2) . . . . ?
C16 C11 C12 C13 0.4(3) . . . . ?
B1 C11 C12 C13 -179.3(2) . . . . ?
C16 C11 C12 C1 -179.9(2) . . . . ?
B1 C11 C12 C1 0.4(4) . . . . ?
C11 C12 C13 C14 -1.2(4) . . . . ?
C1 C12 C13 C14 179.1(2) . . . . ?
C12 C13 C14 C15 0.7(4) . . . . ?
C13 C14 C15 C16 0.5(4) . . . . ?
C14 C15 C16 C11 -1.3(4) . . . . ?
C12 C11 C16 C15 0.9(4) . . . . ?
B1 C11 C16 C15 -179.4(2) . . . . ?
O1A B1 C21 C26 107.3(5) . . . . ?
O1B B1 C21 C26 79.5(7) . . . . ?
C11 B1 C21 C26 -84.2(3) . . . . ?
O1A B1 C21 C22 -76.7(5) . . . . ?
O1B B1 C21 C22 -104.5(7) . . . . ?
C11 B1 C21 C22 91.8(3) . . . . ?
C26 C21 C22 C23 1.0(3) . . . . ?
B1 C21 C22 C23 -175.0(2) . . . . ?
C26 C21 C22 C27 178.0(2) . . . . ?
B1 C21 C22 C27 1.9(3) . . . . ?
C21 C22 C23 C24 1.3(4) . . . . ?
C27 C22 C23 C24 -175.6(3) . . . . ?
C22 C23 C24 C25 -2.4(5) . . . . ?
C22 C23 C24 C28 177.2(3) . . . . ?
C23 C24 C25 C26 1.0(4) . . . . ?
C28 C24 C25 C26 -178.5(3) . . . . ?
C24 C25 C26 C21 1.3(4) . . . . ?
C24 C25 C26 C29 -178.0(3) . . . . ?
C22 C21 C26 C25 -2.3(3) . . . . ?
B1 C21 C26 C25 173.8(2) . . . . ?
C22 C21 C26 C29 177.0(2) . . . . ?
B1 C21 C26 C29 -6.9(3) . . . . ?
