Electrochemical 5-exo-dig aza-cyclization of 2-alkynylbenzamides toward 3-hydroxyisoindolinone derivatives
Zhaojiang, Shi; Li, Nan; Wang, Wei-Zhen; Lu, Hao-Kuan; Yuan, Yaofeng; Li, Zhen; Ye, Ke-Yin; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB00637E

data_7158690
_publ_section_title
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 Electrochemical 5-exo-dig aza-cyclization of 2-alkynylbenzamides toward
 3-hydroxyisoindolinone derivatives
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00637E
_journal_year                    2022
_chemical_formula_moiety         'C15 H11 Br O3'
_chemical_formula_sum            'C15 H11 Br O3'
_chemical_formula_weight         319.15
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-09-11
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-10-13 deposited with the CCDC.	2022-05-09 downloaded from the CCDC.
;
_cell_angle_alpha                91.227(3)
_cell_angle_beta                 91.751(3)
_cell_angle_gamma                113.005(2)
_cell_formula_units_Z            2
_cell_length_a                   6.8870(4)
_cell_length_b                   8.0452(6)
_cell_length_c                   12.4860(10)
_cell_measurement_reflns_used    5433
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      29.006
_cell_measurement_theta_min      3.150
_cell_volume                     636.08(8)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.760
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0685
_diffrn_reflns_av_unetI/netI     0.0818
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.760
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17388
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.760
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.316
_diffrn_reflns_theta_min         2.752
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    3.231
_exptl_absorpt_correction_T_max  0.7468
_exptl_absorpt_correction_T_min  0.4517
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1646 before and 0.0736 after correction.
The Ratio of minimum to maximum transmission is 0.6048.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.666
_exptl_crystal_description       plate
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.882
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         4043
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.1005
_refine_ls_R_factor_gt           0.0467
_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^)+(0.0464P)^2^+0.0815P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1145
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2508
_reflns_number_total             4043
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00637e2.cif
_cod_data_source_block           ln-22n-1
_cod_database_code               7158690
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.738
_shelx_estimated_absorpt_t_min   0.564
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H008), C8(H00E)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H00A), C12(H00C), C3(H00D), C14(H00F), C15(H00G), C11(H00H), C5(H00I),
 C4(H00J)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H003)
;
_shelx_res_checksum              89260
_olex2_submission_special_instructions 'No special instructions were received'