Catalyst- and oxidant-free electrooxidative site-selective [3/4 + 2] annulation to fused polycyclic heteroaromatics
Guan, Wenjing; Ying, Ke; Yuan, Chengcheng; Hang, Jinlin; Liu, Chengkou; Huang, Xiangxing; Fang, Zheng; Guo, Kai; Green Chemistry 24 (2022) 5191–5196; doi:10.1039/D2GC01248K

data_7245027
_publ_section_title
;
 Catalyst- and oxidant-free electrooxidative site-selective [3/4 + 2]
 annulation to fused polycyclic heteroaromatics
;
_journal_issue                   13
_journal_name_full               'Green Chemistry'
_journal_page_first              5191
_journal_page_last               5196
_journal_paper_doi               10.1039/D2GC01248K
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C23 H18 N2 O'
_chemical_formula_sum            'C23 H18 N2 O'
_chemical_formula_weight         338.39
_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             2021-08-04
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-01-04 deposited with the CCDC.	2022-05-24 downloaded from the CCDC.
;
_cell_angle_alpha                74.368(2)
_cell_angle_beta                 81.158(2)
_cell_angle_gamma                83.467(2)
_cell_formula_units_Z            2
_cell_length_a                   8.1325(4)
_cell_length_b                   9.3708(5)
_cell_length_c                   11.6459(7)
_cell_measurement_reflns_used    3628
_cell_measurement_temperature    193
_cell_measurement_theta_max      29.930
_cell_measurement_theta_min      2.520
_cell_volume                     842.08(8)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      193
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_unetI/netI     0.0623
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9842
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.022
_diffrn_reflns_theta_min         2.520
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6423
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1752 before and 0.0922 after correction.
The Ratio of minimum to maximum transmission is 0.8610.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4853
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0772
_refine_ls_R_factor_gt           0.0529
_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^)+(0.0638P)^2^+0.2068P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1291
_refine_ls_wR_factor_ref         0.1481
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3545
_reflns_number_total             4853
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc01248k2.cif
_cod_data_source_block           a
_cod_depositor_comments          'Adding full bibliography for 7245027.cif.'
_cod_database_code               7245027
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.990
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C6(H6), C7(H7), C4(H4), C13(H13), C23(H23), C19(H19), C14(H14),
 C21(H21), C22(H22), C20(H20), C3(H3)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C1(H1A,H1B,H1C)
;
_shelx_res_checksum              39767
_shelx_hkl_checksum              46196
_olex2_submission_special_instructions 'No special instructions were received'