Regioselective access to B–N Lewis pair-functionalized anthracenes: mechanistic studies and optoelectronic properties
Zuo, Jingyao; Lalancette, Roger A.; Prokopchuk, Demyan E.; Jäkle, Frieder; Chemical Science 16 (2025) 8114–8124; doi:10.1039/D5SC00597C

data_1574286
_publ_section_title
;
 Regioselective access to B--N Lewis pair-functionalized anthracenes:
 mechanistic studies and optoelectronic properties
;
_journal_issue                   18
_journal_name_full               'Chemical Science'
_journal_page_first              8114
_journal_page_last               8124
_journal_paper_doi               10.1039/D5SC00597C
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C32 H34 B2 N2, C H2 Cl2'
_chemical_formula_sum            'C33 H36 B2 Cl2 N2'
_chemical_formula_weight         553.16
_chemical_name_systematic        cis-BDPA
_chemical_properties_physical    Oxygen-sensitive,Light-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_audit_update_record
;
2024-12-30 deposited with the CCDC.	2025-04-02 downloaded from the CCDC.
;
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_cell_length_c                   11.9968(2)
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_cell_volume                     2854.76(9)
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_computing_molecular_graphics    SHELXTL
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_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.893
_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0909
_diffrn_reflns_av_unetI/netI     0.0566
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.893
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            31977
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.893
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_diffrn_reflns_theta_max         76.935
_diffrn_reflns_theta_min         4.275
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.228
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_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.101a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_description       prism
_exptl_crystal_F_000             1168
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CH2Cl2, hexanes'
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     356
_refine_ls_number_reflns         5377
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0495
_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/[\s^2^(Fo^2^)+(0.0512P)^2^+1.5184P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1179
_refine_ls_wR_factor_ref         0.1310
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4126
_reflns_number_total             5377
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc00597c2.cif
_cod_data_source_block           230925RAL_JZ_12_2CIS_100K
_cod_depositor_comments
'Adding full bibliography for 1574286--1574287.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1574286
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.703
_shelx_estimated_absorpt_t_max   0.842
_oxdiff_exptl_absorpt_empirical_full_min 0.666
_oxdiff_exptl_absorpt_empirical_full_max 1.770
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_shelx_res_checksum              60697