Use of tailored boronic acids both as a radical donor and acceptor in a visible light-mediated di-functionalization of maleimides: rapid access to fused benzo[<i>e</i>]isoindole-1,3-diones.
Manna, Sabyasachi; Sreedhara, Rahul Halanuru; Punesh, Thanay Umesh; Prabhu, Kandikere Ramaiah; Chemical communications (Cambridge, England) 61 (2025) 17669–17672; doi:10.1039/d5cc04449a

data_7135083
_publ_section_title
;
 Use of tailored boronic acids both as a radical donor and acceptor in a
 visible light-mediated di-functionalization of maleimides: rapid access
 to fused benzo[<i>e</i>]isoindole-1,3-diones.
;
_journal_issue                   90
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              17669
_journal_page_last               17672
_journal_paper_doi               10.1039/d5cc04449a
_journal_volume                  61
_journal_year                    2025
_chemical_absolute_configuration rm
_chemical_formula_sum            'C22 H23 N O2'
_chemical_formula_weight         333.41
_chemical_name_systematic
2-(2-(tert-butyl)phenyl)-3a,4,5,9b-tetrahydro-1H-benzo[e]isoindole-1,3(2H)-dione
_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   mixed
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2024-09-16 deposited with the CCDC.	2025-10-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5410(4)
_cell_length_b                   12.2915(5)
_cell_length_c                   17.0269(6)
_cell_measurement_reflns_used    9213
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      2.67
_cell_volume                     1787.51(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX4'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            65584
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.314
_diffrn_reflns_theta_min         2.904
_exptl_absorpt_coefficient_mu    0.079
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             712
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetonitrile'
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 1736 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4441
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.161
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0500
_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^)+(0.0763P)^2^+0.4068P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1307
_refine_ls_wR_factor_ref         0.1318
_reflns_Friedel_coverage         0.757
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                4333
_reflns_number_total             4441
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc04449a3.cif
_cod_data_source_block           HSRM_128_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_absolute_configuration' value 'RM' was changed
to 'rm' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7135083.cif.
;
_cod_database_code               7135083
_shelx_shelxl_version_number     2019/1
_shelx_res_checksum              98939
_shelx_hkl_checksum              34208