#------------------------------------------------------------------------------
#$Date: 2026-02-28 02:28:36 +0100 (Sat 28 de Feb de 2026) $
#$Revision: 304661 $
#$URL: svn://www.crystallography.net/cod/cif/7/72/03/7720374.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_7720374
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         'C16 H8 Br2'
_chemical_formula_sum            'C16 H8 Br2'
_chemical_formula_weight         360.04
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_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            2
_cell_length_a                   11.4659(4)
_cell_length_b                   14.2304(4)
_cell_length_c                   3.93254(13)
_cell_measurement_reflns_used    4043
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.8190
_cell_measurement_theta_min      3.4030
_cell_volume                     641.65(4)
_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_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 1.000
_diffrn_measured_fraction_theta_max 0.998
_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  0.0370
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            7931
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.893
_diffrn_reflns_theta_min         2.281
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_exptl_absorpt_coefficient_mu    6.293
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22204
_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    1.864
_exptl_crystal_description       'elongated prism'
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.065(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     83
_refine_ls_number_reflns         1534
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0228
_refine_ls_R_factor_gt           0.0205
_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/[σ²(Fo²)+(0.0256P)²+0.1616P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0501
_refine_ls_wR_factor_ref         0.0518
_reflns_Friedel_coverage         0.635
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1450
_reflns_number_total             1534
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d6dt00412a2.cif
_cod_data_source_block           S6_wa3657_sm308
_cod_database_code               7720374
_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   0.238
_shelx_estimated_absorpt_t_max   0.704
_shelx_res_file
;
TITL wa3657=sm308 in P2(1)2(1)2 at -100C CAP+erm
    fin.res
    created by SHELXL-2019/3 at 12:24:07 on 15-Nov-2024
CELL 0.71073  11.46594  14.23039   3.93254  90.0000  90.0000  90.0000
ZERR    2.00   0.00040   0.00041   0.00013   0.0000   0.0000   0.0000
LATT -1
SYMM -X,-Y,+Z
SYMM 0.5-X,0.5+Y,-Z
SYMM 0.5+X,0.5-Y,-Z
SFAC C H Br
UNIT 32 16 4

TEMP -100
SIZE 0.075 0.06 0.32
REM colourless elongated prism

ACTA
L.S. 10
FMAP 2
PLAN 10
CONF
BOND $H
TWIN -1 0 0 0 -1 0 0 0 -1 2

WGHT    0.025600    0.161600
BASF   0.06517
FVAR       0.52228
BR1   3    0.844960    0.405620    0.499240    11.00000    0.03190    0.02432 =
         0.03327   -0.00141   -0.00415   -0.00246
C1    1    0.768493    0.296456    0.338474    11.00000    0.02522    0.01869 =
         0.02183    0.00182    0.00321   -0.00048
C2    1    0.654949    0.302907    0.210120    11.00000    0.02236    0.01854 =
         0.02360    0.00341    0.00482    0.00345
C3    1    0.602696    0.221312    0.088354    11.00000    0.02619    0.02313 =
         0.02843    0.00235    0.00102   -0.00015
AFIX  43
H3    2    0.525850    0.224001   -0.001440    11.00000   -1.20000
AFIX   0
C4    1    0.661469    0.135973    0.096425    11.00000    0.03933    0.01824 =
         0.03402   -0.00016    0.00484   -0.00180
AFIX  43
H4    2    0.625043    0.080961    0.010109    11.00000   -1.20000
AFIX   0
C5    1    0.773033    0.130924    0.230016    11.00000    0.03313    0.01717 =
         0.04200    0.00457    0.01028    0.00625
AFIX  43
H5    2    0.812634    0.072337    0.239053    11.00000   -1.20000
AFIX   0
C6    1    0.827062    0.211984    0.351145    11.00000    0.02478    0.02758 =
         0.02985    0.00588    0.00501    0.00587
AFIX  43
H6    2    0.903765    0.209032    0.441860    11.00000   -1.20000
AFIX   0
C7    1    0.591640    0.389867    0.205901    11.00000    0.02224    0.02197 =
         0.02877    0.00253    0.00080    0.00165
C8    1    0.533453    0.459554    0.204806    11.00000    0.02234    0.02040 =
         0.03064   -0.00096    0.00004    0.00138
HKLF 4




REM  wa3657=sm308 in P2(1)2(1)2 at -100C CAP+erm
REM wR2 = 0.0518, GooF = S = 1.059, Restrained GooF = 1.059 for all data
REM R1 = 0.0205 for 1450 Fo > 4sig(Fo) and 0.0228 for all 1534 data
REM 83 parameters refined using 0 restraints

END

WGHT      0.0256      0.1616

REM Highest difference peak  0.411,  deepest hole -0.236,  1-sigma level  0.061
Q1    1   0.8412  0.3511  0.4867  11.00000  0.05    0.41
Q2    1   0.7857  0.4381  0.4889  11.00000  0.05    0.32
Q3    1   0.9004  0.3922  0.3116  11.00000  0.05    0.26
Q4    1   0.7846  0.4022  0.6999  11.00000  0.05    0.26
Q5    1   0.6436  0.2608  0.1110  11.00000  0.05    0.25
Q6    1   0.6492  0.1828  0.0666  11.00000  0.05    0.25
Q7    1   0.8933  0.4016  0.7001  11.00000  0.05    0.24
Q8    1   0.8997  0.3739  0.6658  11.00000  0.05    0.24
Q9    1   0.7118  0.2993  0.2387  11.00000  0.05    0.22
Q10   1   0.5318  0.3991  0.1625  11.00000  0.05    0.22
;
_shelx_res_checksum              57966
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'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
Br1 Br 0.84496(2) 0.40562(2) 0.49924(9) 0.02983(11) Uani 1 1 d . . . . .
C1 C 0.7685(3) 0.29646(19) 0.3385(7) 0.0219(6) Uani 1 1 d . . . . .
C2 C 0.6549(3) 0.30291(18) 0.2101(7) 0.0215(6) Uani 1 1 d . . . . .
C3 C 0.6027(3) 0.2213(2) 0.0884(7) 0.0259(6) Uani 1 1 d . . . . .
H3 H 0.525850 0.224001 -0.001440 0.031 Uiso 1 1 calc R U . . .
C4 C 0.6615(3) 0.1360(2) 0.0964(8) 0.0305(7) Uani 1 1 d . . . . .
H4 H 0.625043 0.080961 0.010109 0.037 Uiso 1 1 calc R U . . .
C5 C 0.7730(3) 0.1309(2) 0.2300(9) 0.0308(7) Uani 1 1 d . . . . .
H5 H 0.812634 0.072337 0.239053 0.037 Uiso 1 1 calc R U . . .
C6 C 0.8271(3) 0.2120(2) 0.3511(8) 0.0274(6) Uani 1 1 d . . . . .
H6 H 0.903765 0.209032 0.441860 0.033 Uiso 1 1 calc R U . . .
C7 C 0.5916(3) 0.3899(2) 0.2059(8) 0.0243(6) Uani 1 1 d . . . . .
C8 C 0.5335(3) 0.4596(2) 0.2048(8) 0.0245(6) Uani 1 1 d . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.03190(16) 0.02432(15) 0.03327(17) -0.00141(18) -0.0042(2) -0.00246(10)
C1 0.0252(14) 0.0187(13) 0.0218(13) 0.0018(11) 0.0032(11) -0.0005(11)
C2 0.0224(13) 0.0185(12) 0.0236(13) 0.0034(11) 0.0048(12) 0.0034(11)
C3 0.0262(14) 0.0231(12) 0.0284(16) 0.0024(11) 0.0010(10) -0.0001(12)
C4 0.0393(18) 0.0182(13) 0.0340(16) -0.0002(12) 0.0048(13) -0.0018(13)
C5 0.0331(17) 0.0172(13) 0.0420(18) 0.0046(14) 0.0103(15) 0.0062(12)
C6 0.0248(15) 0.0276(14) 0.0299(14) 0.0059(13) 0.0050(12) 0.0059(12)
C7 0.0222(14) 0.0220(13) 0.0288(14) 0.0025(12) 0.0008(11) 0.0016(11)
C8 0.0223(14) 0.0204(13) 0.0306(14) -0.0010(12) 0.0000(12) 0.0014(12)
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'
Br Br -0.2901 2.4595 '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
C6 C1 C2 121.6(3) . . ?
C6 C1 Br1 118.6(2) . . ?
C2 C1 Br1 119.8(2) . . ?
C3 C2 C1 118.0(3) . . ?
C3 C2 C7 119.9(3) . . ?
C1 C2 C7 122.1(3) . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 119.8(3) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 119.6(3) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C8 C7 C2 176.4(3) . . ?
C7 C8 C8 179.7(4) . 2_665 ?
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
Br1 C1 1.893(3) . ?
C1 C6 1.378(4) . ?
C1 C2 1.399(4) . ?
C2 C3 1.392(4) . ?
C2 C7 1.435(4) . ?
C3 C4 1.389(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.393(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.195(4) . ?
C8 C8 1.383(6) 2_665 ?
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
C6 C1 C2 C3 -1.2(4) . . . . ?
Br1 C1 C2 C3 178.8(2) . . . . ?
C6 C1 C2 C7 177.9(3) . . . . ?
Br1 C1 C2 C7 -2.2(4) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C7 C2 C3 C4 -178.7(3) . . . . ?
C2 C3 C4 C5 0.7(4) . . . . ?
C3 C4 C5 C6 -1.1(5) . . . . ?
C2 C1 C6 C5 0.8(4) . . . . ?
Br1 C1 C6 C5 -179.2(2) . . . . ?
C4 C5 C6 C1 0.4(5) . . . . ?
