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_7242055
_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 H20 N2 O2'
_chemical_formula_sum            'C24 H20 N2 O2'
_chemical_formula_weight         368.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-12-11
_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                90
_cell_angle_beta                 102.461(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6666(5)
_cell_length_b                   23.4805(11)
_cell_length_c                   9.5853(4)
_cell_measurement_reflns_used    1862
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.4740
_cell_measurement_theta_min      3.7500
_cell_volume                     1904.62(17)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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      3.00  35.00   1.00    1.15    --  -33.50  77.00 -90.00   32
  2  \w   -102.00 -59.00   1.00    1.15    --  -33.50 -57.00 120.00   43
  3  \w    -63.00 -37.00   1.00    1.15    --  -33.50 178.00 120.00   26
  4  \w    -58.00 -15.00   1.00    1.15    --  -33.50  77.00 -90.00   43
  5  \w    -47.00 -17.00   1.00    1.15    --  -33.50 -57.00 120.00   30
  6  \w     42.00  75.00   1.00    1.15    --   36.47 -99.00 -30.00   33
  7  \w     -2.00  25.00   1.00    1.15    --   36.47 -99.00 -30.00   27
  8  \w     75.00 101.00   1.00    1.15    --   36.47 178.00  30.00   26
  9  \w     57.00 110.00   1.00    1.15    --   36.47 178.00 -60.00   53
 10  \w     41.00 103.00   1.00    1.15    --   36.47  57.00  30.00   62
 11  \w    109.00 151.00   1.00    5.50    --  108.00  61.00 -30.00   42
 12  \w     79.00 176.00   1.00    5.50    --  108.00  77.00-180.00   97
 13  \w     79.00 177.00   1.00    5.50    --  108.00  77.00 -90.00   98
 14  \w     57.00 110.00   1.00    5.50    --  108.00 -94.00   0.00   53
 15  \w     40.00  96.00   1.00    5.50    --  108.00 -94.00  90.00   56
 16  \w     88.00 150.00   1.00    5.50    --  108.00  61.00-120.00   62
 17  \w     37.00 111.00   1.00    5.50    --  108.00-111.00-120.00   74
 18  \w    103.00 178.00   1.00    5.50    --  108.00 111.00 150.00   75
;
_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      -0.1791100000
_diffrn_orient_matrix_UB_12      -0.0031407000
_diffrn_orient_matrix_UB_13      -0.0074470000
_diffrn_orient_matrix_UB_21      -0.0057909000
_diffrn_orient_matrix_UB_22      0.0652730000
_diffrn_orient_matrix_UB_23      0.0139101000
_diffrn_orient_matrix_UB_31      -0.0321006000
_diffrn_orient_matrix_UB_32      0.0056968000
_diffrn_orient_matrix_UB_33      -0.1639258000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7573
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.044
_diffrn_reflns_theta_max         67.043
_diffrn_reflns_theta_min         3.765
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.656
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94649
_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    1.285
_exptl_crystal_description       prism
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3403
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0517
_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^)+(0.0723P)^2^+0.2939P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1347
_refine_ls_wR_factor_ref         0.1502
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2558
_reflns_number_total             3403
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0gc03930f2.cif
_cod_data_source_block           201912314
_cod_depositor_comments
'Adding full bibliography for 7242054--7242055.cif.'
_cod_original_cell_volume        1904.62(18)
_cod_database_code               7242055
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C40H40O2N4
_shelx_estimated_absorpt_t_max   0.937
_shelx_estimated_absorpt_t_min   0.891
_reflns_odcompleteness_completeness 99.97
_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
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C15(H15), C16(H16), C17(H17), C18(H18),
 C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              89919
_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 1.127
_oxdiff_exptl_absorpt_empirical_full_min 0.919