One tool to bring them all: Au-catalyzed synthesis of B,O- and B,N-doped PAHs from boronic and borinic acids
Ouadoudi, Omar; Kaehler, Tanja; Bolte, Michael; Lerner, Hans-Wolfram; Wagner, Matthias; Chemical Science 12 (2021) 5898–5909; doi:10.1039/D1SC00543J

data_1561086
_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 B N'
_chemical_formula_sum            'C28 H32 B N'
_chemical_formula_weight         393.35
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-01-26 deposited with the CCDC.	2021-03-17 downloaded from the CCDC.
;
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_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_length_b                   11.8608(7)
_cell_length_c                   20.7807(9)
_cell_measurement_reflns_used    16025
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.03
_cell_measurement_theta_min      3.39
_cell_volume                     2316.8(2)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            16025
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_min         3.390
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.498
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.128
_exptl_crystal_description       plate
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
; 
 Flack x determined using 1430 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   2.9(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.249
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         4083
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.281
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0662
_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^)+(0.0468P)^2^+1.8350P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1517
_refine_ls_wR_factor_ref         0.1551
_reflns_Friedel_coverage         0.749
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3825
_reflns_number_total             4083
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc00543j2.cif
_cod_data_source_block           wa2862
_cod_depositor_comments
'Adding full bibliography for 1561085--1561097.cif.'
_cod_database_code               1561086
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.986
_shelx_estimated_absorpt_t_max   0.994
_shelx_res_checksum              11727
_shelx_hkl_checksum              85299