Metal-free C(sp3)–H functionalization (C–C and C–N bond formation) of 1,2,3,4-tetrahydroacridines using deep eutectic solvents as catalyst and reaction medium
Shirisha, Thangellapally; Majhi, Subir; Balasubramanian, Sridhar; Kashinath, Dhurke; Organic & Biomolecular Chemistry 22 (2024) 1434–1440; doi:10.1039/D3OB01752D

data_7159775
_publ_section_title
;
 Metal-free C(sp3)--H functionalization (C--C and C--N bond formation) of
 1,2,3,4-tetrahydroacridines using deep eutectic solvents as catalyst and
 reaction medium
;
_journal_issue                   7
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              1434
_journal_page_last               1440
_journal_paper_doi               10.1039/D3OB01752D
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C23 H18 Br Cl N2 O2'
_chemical_formula_sum            'C23 H18 Br Cl N2 O2'
_chemical_formula_weight         469.75
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-09-14 deposited with the CCDC.	2024-01-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
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_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_length_c                   18.9108(8)
_cell_measurement_reflns_used    9945
_cell_measurement_temperature    294(2)
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_cell_measurement_theta_min      2.221
_cell_volume                     1999.19(14)
_computing_cell_refinement       '<i>SAINT</i> (Bruker, 2016)'
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_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
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_diffrn_ambient_temperature      294(2)
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_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_av_unetI/netI     0.0599
_diffrn_reflns_Laue_measured_fraction_full 0.997
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_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
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_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            36237
_diffrn_reflns_point_group_measured_fraction_full 0.997
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_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.526
_diffrn_reflns_theta_min         2.221
_exptl_absorpt_coefficient_mu    2.212
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.4776
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
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_exptl_crystal_description       block
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_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.855
_refine_diff_density_min         -0.724
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         6068
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0434
_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^)+(0.0418P)^2^+0.8782P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0986
_refine_ls_wR_factor_ref         0.1175
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3860
_reflns_number_total             6068
_reflns_threshold_expression     'I > 2\s(I)'
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_cod_data_source_block           KB1033_0m
_cod_depositor_comments          'Adding full bibliography for 7159775.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7159775
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.576
_shelx_estimated_absorpt_t_max   0.666
_shelx_res_checksum              6818