An oxidant- and catalyst-free electrooxidative cross-coupling approach to 3-tetrahydroisoquinoline substituted coumarins
Kong, Yanyan; Kim, Jung Keun; Li, Yabo; Zhang, Jianye; Huang, Mengmeng; Wu, Yangjie; Green Chemistry 23 (2021) 1274–1279; doi:10.1039/D0GC03930F

data_7242054
_publ_section_title
;
 An oxidant- and catalyst-free electrooxidative cross-coupling approach to
 3-tetrahydroisoquinoline substituted coumarins
;
_journal_issue                   3
_journal_name_full               'Green Chemistry'
_journal_page_first              1274
_journal_page_last               1279
_journal_paper_doi               10.1039/D0GC03930F
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C24 H19 N O3'
_chemical_formula_sum            'C24 H19 N O3'
_chemical_formula_weight         369.40
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-10-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-09-17 deposited with the CCDC.	2021-01-08 downloaded from the CCDC.
;
_cell_angle_alpha                69.761(7)
_cell_angle_beta                 87.356(6)
_cell_angle_gamma                78.198(6)
_cell_formula_units_Z            4
_cell_length_a                   9.0990(6)
_cell_length_b                   12.6543(9)
_cell_length_c                   17.4953(14)
_cell_measurement_reflns_used    3203
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.2790
_cell_measurement_theta_min      3.8080
_cell_volume                     1849.4(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -62.00  36.00   1.00    1.50    --  -33.50  77.00-120.00   98
  2  \w   -102.00 -24.00   1.00    1.50    --  -33.50 -57.00 120.00   78
  3  \w     73.00  99.00   1.00    1.50    --   36.47  57.00  90.00   26
  4  \w    -33.00  57.00   1.00    1.50    --   36.47 -37.00-180.00   90
  5  \w     -4.00  77.00   1.00    1.50    --   36.47 -99.00 -30.00   81
  6  \w      8.00  67.00   1.00    1.50    --   36.47  77.00  90.00   59
  7  \w     31.00  59.00   1.00    1.50    --   36.47  57.00  90.00   28
  8  \w     10.00  39.00   1.00    1.50    --   36.47 -99.00 150.00   29
  9  \w     72.00  97.00   1.00    1.50    --   36.47  77.00  90.00   25
 10  \w     62.00  90.00   1.00    1.50    --   36.47 178.00 150.00   28
 11  \w     41.00  67.00   1.00    1.50    --   36.47 -99.00 150.00   26
 12  \w     59.00 103.00   1.00    1.50    --   36.47  57.00   0.00   44
 13  \w    -19.00   7.00   1.00    1.50    --   36.47 -37.00 -60.00   26
 14  \w     12.00  52.00   1.00    1.50    --   36.47 -57.00 150.00   40
 15  \w      5.00  31.00   1.00    1.50    --   36.47 -37.00   0.00   26
 16  \w    111.00 137.00   1.00    7.50    --  108.00  77.00 -90.00   26
 17  \w     79.00 108.00   1.00    7.50    --  108.00-111.00 -90.00   29
 18  \w    105.00 177.00   1.00    7.50    --  108.00  30.00-150.00   72
 19  \w     65.00 128.00   1.00    7.50    --  108.00 -45.00  60.00   63
 20  \w    147.00 173.00   1.00    7.50    --  108.00 105.00 100.00   26
 21  \w     89.00 176.00   1.00    7.50    --  108.00  61.00 150.00   87
 22  \w    101.00 132.00   1.00    7.50    --  108.00 105.00 100.00   31
 23  \w    103.00 162.00   1.00    7.50    --  108.00  45.00  90.00   59
 24  \w     45.00 128.00   1.00    7.50    --  108.00 -45.00   0.00   83
 25  \w     39.00 124.00   1.00    7.50    --  108.00 -45.00-120.00   85
 26  \w     67.00 122.00   1.00    7.50    --  108.00 -61.00 150.00   55
 27  \w     54.00 102.00   1.00    7.50    --  108.00 -94.00-180.00   48
 28  \w     37.00 111.00   1.00    7.50    --  108.00-111.00  60.00   74
 29  \w     57.00 110.00   1.00    7.50    --  108.00 -94.00 -60.00   53
 30  \w     50.00 109.00   1.00    7.50    --  108.00 -94.00  90.00   59
 31  \w     37.00 115.00   1.00    7.50    --  108.00 -30.00 150.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1130120000
_diffrn_orient_matrix_UB_12      0.1013137000
_diffrn_orient_matrix_UB_13      -0.0573328000
_diffrn_orient_matrix_UB_21      0.0422770000
_diffrn_orient_matrix_UB_22      -0.0470612000
_diffrn_orient_matrix_UB_23      -0.0700700000
_diffrn_orient_matrix_UB_31      -0.1240184000
_diffrn_orient_matrix_UB_32      -0.0711826000
_diffrn_orient_matrix_UB_33      0.0248474000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12884
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.070
_diffrn_reflns_theta_max         67.070
_diffrn_reflns_theta_min         3.801
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.704
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90406
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       prism
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     513
_refine_ls_number_reflns         6584
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0512
_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^+0.1160P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1315
_refine_ls_wR_factor_ref         0.1504
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4920
_reflns_number_total             6584
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0gc03930f2.cif
_cod_data_source_block           201909249
_cod_depositor_comments
'Adding full bibliography for 7242054--7242055.cif.'
_cod_original_cell_volume        1849.4(2)
_cod_database_code               7242054
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H20O4N1S
_shelx_estimated_absorpt_t_max   0.933
_shelx_estimated_absorpt_t_min   0.890
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 H3'A-O3'
 0.9 with sigma of 0.02
 H3A-O3
 0.9 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C10(H10), C10'(H10')
3.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B), C17'(H17C,H17D), C18'(H18C,H18D)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C12(H12), C13(H13), C14(H14), C15(H15),
 C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C1'(H1'), C2'(H2'), C3'(H3'),
  C4'(H4'), C12'(H12'), C13'(H13'), C14'(H14'), C15'(H15'), C20'(H20'),
 C21'(H21'), C22'(H22'), C23'(H23'), C24'(H24')
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.367
_oxdiff_exptl_absorpt_empirical_full_min 0.860