#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:15:59 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301787 $
#$URL: svn://www.crystallography.net/cod/cif/1/56/10/1561089.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_1561089
loop_
_publ_author_name
'Ouadoudi, Omar'
'Kaehler, Tanja'
'Bolte, Michael'
'Lerner, Hans-Wolfram'
'Wagner, Matthias'
_publ_section_title
;
 One tool to bring them all: Au-catalyzed synthesis of B,O- and B,N-doped
 PAHs from boronic and borinic acids
;
_journal_issue                   16
_journal_name_full               'Chemical Science'
_journal_page_first              5898
_journal_page_last               5909
_journal_paper_doi               10.1039/D1SC00543J
_journal_volume                  12
_journal_year                    2021
_chemical_formula_moiety         'C28 H32 B4 O6'
_chemical_formula_sum            'C28 H32 B4 O6'
_chemical_formula_weight         507.77
_space_group_crystal_system      tetragonal
_space_group_IT_number           86
_space_group_name_Hall           '-P 4bc'
_space_group_name_H-M_alt        'P 42/n :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-03-05 deposited with the CCDC.	2021-03-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.5614(14)
_cell_length_b                   19.5614(14)
_cell_length_c                   6.7125(5)
_cell_measurement_reflns_used    6894
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.16
_cell_measurement_theta_min      3.22
_cell_volume                     2568.5(3)
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  SHELXL
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1287
_diffrn_reflns_av_unetI/netI     0.0628
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            12813
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.008
_diffrn_reflns_theta_min         3.209
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.632
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       needle
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.265
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2266
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.265
_refine_ls_R_factor_all          0.1878
_refine_ls_R_factor_gt           0.1169
_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)+14.8542P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1815
_refine_ls_wR_factor_ref         0.2140
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1422
_reflns_number_total             2266
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc00543j2.cif
_cod_data_source_block           wa2898
_cod_depositor_comments
'Adding full bibliography for 1561085--1561097.cif.'
_cod_original_cell_volume        2568.5(4)
_cod_original_sg_symbol_H-M      'P 42/n'
_cod_database_code               1561089
_shelx_shelxl_version_number     2018/3
_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   0.990
_shelx_estimated_absorpt_t_max   0.997
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-y, x+1/2, z+1/2'
'y+1/2, -x, z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'y, -x-1/2, -z-1/2'
'-y-1/2, x, -z-1/2'
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 0.3162(3) 0.7141(3) 0.5187(10) 0.0159(13) Uani 1 1 d . . . . .
B2 B 0.5051(3) 0.6752(3) 0.5131(11) 0.0227(15) Uani 1 1 d . . . . .
O1 O 0.37858(18) 0.68105(19) 0.5174(6) 0.0214(9) Uani 1 1 d . . . . .
O2 O 0.56871(19) 0.70450(19) 0.4920(8) 0.0317(11) Uani 1 1 d . . . . .
O3 O 0.50809(19) 0.60553(19) 0.5347(6) 0.0248(10) Uani 1 1 d . . . . .
C1 C 0.3141(3) 0.7926(3) 0.5164(8) 0.0153(11) Uani 1 1 d . . . . .
C2 C 0.2510(3) 0.8296(3) 0.5179(8) 0.0165(12) Uani 1 1 d . . . . .
C3 C 0.2535(3) 0.9002(3) 0.5177(9) 0.0199(12) Uani 1 1 d . . . . .
H3 H 0.212000 0.925364 0.518939 0.024 Uiso 1 1 calc R U . . .
C4 C 0.3160(3) 0.9356(3) 0.5155(9) 0.0245(14) Uani 1 1 d . . . . .
H4 H 0.316428 0.984171 0.515741 0.029 Uiso 1 1 calc R U . . .
C5 C 0.3770(3) 0.8997(3) 0.5131(9) 0.0222(13) Uani 1 1 d . . . . .
H5 H 0.419112 0.923834 0.510671 0.027 Uiso 1 1 calc R U . . .
C6 C 0.3770(3) 0.8279(3) 0.5143(9) 0.0192(12) Uani 1 1 d . . . . .
C7 C 0.4389(3) 0.7868(3) 0.5125(9) 0.0200(12) Uani 1 1 d . . . . .
H7 H 0.481658 0.809780 0.509450 0.024 Uiso 1 1 calc R U . . .
C8 C 0.4390(3) 0.7182(3) 0.5148(9) 0.0216(13) Uani 1 1 d . . . . .
C9 C 0.6194(3) 0.6516(3) 0.5375(11) 0.0295(15) Uani 1 1 d . . . . .
C10 C 0.5788(3) 0.5840(3) 0.4994(11) 0.0282(14) Uani 1 1 d . . . . .
C11 C 0.6388(4) 0.6601(4) 0.7526(11) 0.0405(18) Uani 1 1 d . . . . .
H11A H 0.672778 0.625512 0.788912 0.061 Uiso 1 1 calc R U . . .
H11B H 0.658141 0.705820 0.773070 0.061 Uiso 1 1 calc R U . . .
H11C H 0.598087 0.654671 0.836275 0.061 Uiso 1 1 calc R U . . .
C12 C 0.6798(3) 0.6618(4) 0.4014(12) 0.049(2) Uani 1 1 d . . . . .
H12A H 0.714416 0.626932 0.429350 0.074 Uiso 1 1 calc R U . . .
H12B H 0.664893 0.657947 0.262489 0.074 Uiso 1 1 calc R U . . .
H12C H 0.699350 0.707321 0.423900 0.074 Uiso 1 1 calc R U . . .
C13 C 0.5966(4) 0.5267(3) 0.6349(11) 0.0411(18) Uani 1 1 d . . . . .
H13A H 0.643915 0.512567 0.610654 0.062 Uiso 1 1 calc R U . . .
H13B H 0.591783 0.541746 0.773531 0.062 Uiso 1 1 calc R U . . .
H13C H 0.565843 0.488118 0.610128 0.062 Uiso 1 1 calc R U . . .
C14 C 0.5816(4) 0.5600(4) 0.2837(11) 0.050(2) Uani 1 1 d . . . . .
H14A H 0.628158 0.544893 0.252061 0.075 Uiso 1 1 calc R U . . .
H14B H 0.549795 0.521821 0.265057 0.075 Uiso 1 1 calc R U . . .
H14C H 0.568794 0.597713 0.195327 0.075 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
O1 B1 C1 119.4(5) . . ?
O1 B1 C2 119.1(5) . 2_565 ?
C1 B1 C2 121.5(5) . 2_565 ?
O3 B2 O2 112.7(5) . . ?
O3 B2 C8 125.3(5) . . ?
O2 B2 C8 122.1(5) . . ?
B1 O1 C8 120.5(4) . . ?
B2 O2 C9 107.2(4) . . ?
B2 O3 C10 108.0(4) . . ?
C6 C1 C2 120.3(5) . . ?
C6 C1 B1 117.7(5) . . ?
C2 C1 B1 122.0(5) . . ?
C3 C2 C1 118.4(5) . . ?
C3 C2 B1 125.0(5) . 2_565 ?
C1 C2 B1 116.5(5) . 2_565 ?
C2 C3 C4 121.6(5) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 120.0(5) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.5(5) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 119.2(5) . . ?
C5 C6 C7 123.6(5) . . ?
C1 C6 C7 117.1(5) . . ?
C8 C7 C6 123.7(5) . . ?
C8 C7 H7 118.2 . . ?
C6 C7 H7 118.2 . . ?
C7 C8 O1 121.5(5) . . ?
C7 C8 B2 123.2(5) . . ?
O1 C8 B2 115.3(5) . . ?
O2 C9 C11 107.0(5) . . ?
O2 C9 C12 108.1(5) . . ?
C11 C9 C12 111.7(6) . . ?
O2 C9 C10 102.7(4) . . ?
C11 C9 C10 112.3(6) . . ?
C12 C9 C10 114.3(6) . . ?
O3 C10 C13 109.8(5) . . ?
O3 C10 C14 106.1(5) . . ?
C13 C10 C14 109.9(6) . . ?
O3 C10 C9 102.1(4) . . ?
C13 C10 C9 114.7(6) . . ?
C14 C10 C9 113.5(6) . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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 O1 1.380(7) . ?
B1 C1 1.536(8) . ?
B1 C2 1.570(8) 2_565 ?
B2 O3 1.372(8) . ?
B2 O2 1.377(7) . ?
B2 C8 1.542(8) . ?
O1 C8 1.389(6) . ?
O2 C9 1.465(7) . ?
O3 C10 1.464(7) . ?
C1 C6 1.411(7) . ?
C1 C2 1.431(7) . ?
C2 C3 1.381(7) . ?
C3 C4 1.405(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.406(8) . ?
C5 H5 0.9500 . ?
C6 C7 1.453(7) . ?
C7 C8 1.341(8) . ?
C7 H7 0.9500 . ?
C9 C11 1.502(10) . ?
C9 C12 1.507(9) . ?
C9 C10 1.564(8) . ?
C10 C13 1.485(9) . ?
C10 C14 1.523(9) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
C1 B1 O1 C8 0.2(8) . . . . ?
C2 B1 O1 C8 179.0(5) 2_565 . . . ?
O3 B2 O2 C9 -10.5(8) . . . . ?
C8 B2 O2 C9 168.7(6) . . . . ?
O2 B2 O3 C10 -8.0(7) . . . . ?
C8 B2 O3 C10 172.9(6) . . . . ?
O1 B1 C1 C6 -0.4(8) . . . . ?
C2 B1 C1 C6 -179.1(5) 2_565 . . . ?
O1 B1 C1 C2 -179.9(5) . . . . ?
C2 B1 C1 C2 1.4(8) 2_565 . . . ?
C6 C1 C2 C3 -0.1(8) . . . . ?
B1 C1 C2 C3 179.4(5) . . . . ?
C6 C1 C2 B1 179.6(5) . . . 2_565 ?
B1 C1 C2 B1 -0.9(7) . . . 2_565 ?
C1 C2 C3 C4 0.1(9) . . . . ?
B1 C2 C3 C4 -179.5(6) 2_565 . . . ?
C2 C3 C4 C5 0.2(9) . . . . ?
C3 C4 C5 C6 -0.5(9) . . . . ?
C4 C5 C6 C1 0.5(9) . . . . ?
C4 C5 C6 C7 -179.8(6) . . . . ?
C2 C1 C6 C5 -0.2(9) . . . . ?
B1 C1 C6 C5 -179.7(6) . . . . ?
C2 C1 C6 C7 -179.9(5) . . . . ?
B1 C1 C6 C7 0.6(8) . . . . ?
C5 C6 C7 C8 179.6(6) . . . . ?
C1 C6 C7 C8 -0.7(9) . . . . ?
C6 C7 C8 O1 0.6(10) . . . . ?
C6 C7 C8 B2 -179.9(6) . . . . ?
B1 O1 C8 C7 -0.3(9) . . . . ?
B1 O1 C8 B2 -179.9(6) . . . . ?
O3 B2 C8 C7 173.4(6) . . . . ?
O2 B2 C8 C7 -5.7(10) . . . . ?
O3 B2 C8 O1 -7.1(9) . . . . ?
O2 B2 C8 O1 173.9(6) . . . . ?
B2 O2 C9 C11 -95.6(6) . . . . ?
B2 O2 C9 C12 144.0(6) . . . . ?
B2 O2 C9 C10 22.8(7) . . . . ?
B2 O3 C10 C13 143.5(6) . . . . ?
B2 O3 C10 C14 -97.7(6) . . . . ?
B2 O3 C10 C9 21.4(6) . . . . ?
O2 C9 C10 O3 -26.4(6) . . . . ?
C11 C9 C10 O3 88.2(6) . . . . ?
C12 C9 C10 O3 -143.2(5) . . . . ?
O2 C9 C10 C13 -145.2(6) . . . . ?
C11 C9 C10 C13 -30.6(8) . . . . ?
C12 C9 C10 C13 98.0(7) . . . . ?
O2 C9 C10 C14 87.3(6) . . . . ?
C11 C9 C10 C14 -158.1(6) . . . . ?
C12 C9 C10 C14 -29.5(8) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168307323
