Combining photoredox catalysis and hydrogen atom transfer for dearomative functionalization of electron rich heteroarenes.
Ji, Peng; Meng, Xiang; Chen, Jing; Gao, Feng; Xu, Hang; Wang, Wei; Chemical science 14 (2023) 3332–3337; doi:10.1039/d3sc00060e

data_1568542
_publ_section_title
;
 Combining photoredox catalysis and hydrogen atom transfer for dearomative
 functionalization of electron rich heteroarenes.
;
_journal_issue                   12
_journal_name_full               'Chemical science'
_journal_page_first              3332
_journal_page_last               3337
_journal_paper_doi               10.1039/d3sc00060e
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C8 H9 Br N2 O2'
_chemical_formula_sum            'C8 H9 Br N2 O2'
_chemical_formula_weight         245.08
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-08-23
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-01-04 deposited with the CCDC.	2023-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.2630(13)
_cell_length_b                   24.954(2)
_cell_length_c                   5.6399(5)
_cell_measurement_reflns_used    6364
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.38
_cell_measurement_theta_min      2.89
_cell_volume                     1866.6(3)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0190
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            11450
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.383
_diffrn_reflns_theta_min         1.632
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.372
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5007
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1059 before and 0.0293 after correction.
The Ratio of minimum to maximum transmission is 0.6717.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.744
_exptl_crystal_description       plate
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1899
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0213
_refine_ls_R_factor_gt           0.0185
_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^)+(0.0244P)^2^+1.3127P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0462
_refine_ls_wR_factor_ref         0.0473
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1743
_reflns_number_total             1899
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc00060e2.cif
_cod_data_source_block           mo_220822peng_0ma
_cod_depositor_comments          'Adding full bibliography for 1568542.cif.'
_cod_database_code               1568542
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.811
_shelx_estimated_absorpt_t_min   0.274
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3B,H3A)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C5(H5), C8(H8)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              60723
_shelx_hkl_checksum              50822
_olex2_submission_special_instructions 'No special instructions were received'