A visible-light-induced photocatalyst-free approach for C-3 dicarbonyl coumarin production.
Xi, Jinhu; Wu, Xinjie; Huang, Mengmeng; Kim, Jung Keun; Zhang, Jianye; Li, Yabo; Wu, Yangjie; Chemical communications (Cambridge, England) 57 (2021) 7308–7311; doi:10.1039/d1cc02399c

data_7128554
_publ_section_title
;
 A visible-light-induced photocatalyst-free approach for C-3 dicarbonyl
 coumarin production.
;
_journal_issue                   59
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              7308
_journal_page_last               7311
_journal_paper_doi               10.1039/d1cc02399c
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C24 H16 O4'
_chemical_formula_sum            'C24 H16 O4'
_chemical_formula_weight         368.37
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2020-09-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-10-13 deposited with the CCDC.	2021-06-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.418(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.224(2)
_cell_length_b                   20.020(2)
_cell_length_c                   10.0058(12)
_cell_measurement_reflns_used    2740
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.0140
_cell_measurement_theta_min      4.4200
_cell_volume                     3818.6(7)
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_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   -107.00 -69.00   1.00    4.50    --  -33.50 178.00 -60.00   38
  2  \w   -102.00 -16.00   1.00    4.50    --  -33.50 -57.00 -90.00   86
  3  \w    -45.00  33.00   1.00    4.50    --  -33.50  57.00  60.00   78
  4  \w     49.00  74.00   1.00    4.50    --   36.47 -99.00   0.00   25
  5  \w     -4.00  31.00   1.00    4.50    --   36.47 -99.00   0.00   35
  6  \w     48.00  74.00   1.00    4.50    --   36.47 -99.00-150.00   26
  7  \w     70.00 110.00   1.00    4.50    --   36.47 178.00-120.00   40
  8  \w    -20.00  10.00   1.00    4.50    --   36.47 -77.00-180.00   30
  9  \w     40.00  65.00   1.00    4.50    --   36.47 -77.00-180.00   25
 10  \w     48.00  97.00   1.00    4.50    --   36.47  57.00-150.00   49
 11  \w     23.00  51.00   1.00    4.50    --   36.47  37.00-180.00   28
 12  \w     42.00 123.00   1.00   10.50    --  108.00 -61.00 -90.00   81
 13  \w     92.00 175.00   1.00   10.50    --  108.00  61.00  30.00   83
 14  \w     93.00 125.00   1.00   10.50    --  108.00 -61.00  90.00   32
 15  \w     78.00 104.00   1.00   10.50    --  108.00 -94.00-180.00   26
 16  \w     96.00 176.00   1.00   10.50    --  108.00  61.00  60.00   80
 17  \w     38.00  66.00   1.00   10.50    --  108.00 -94.00-180.00   28
 18  \w     57.00 145.00   1.00   10.50    --  108.00 178.00-150.00   88
 19  \w     65.00 112.00   1.00   10.50    --  108.00-111.00   0.00   47
 20  \w    141.00 178.00   1.00   10.50    --  108.00  45.00 -60.00   37
 21  \w    100.00 127.00   1.00   10.50    --  108.00  45.00 -60.00   27
;
_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      -0.0419725000
_diffrn_orient_matrix_UB_12      0.0648233000
_diffrn_orient_matrix_UB_13      0.0132696000
_diffrn_orient_matrix_UB_21      0.0648020000
_diffrn_orient_matrix_UB_22      0.0416723000
_diffrn_orient_matrix_UB_23      -0.0235184000
_diffrn_orient_matrix_UB_31      -0.0240016000
_diffrn_orient_matrix_UB_32      -0.0007717000
_diffrn_orient_matrix_UB_33      -0.1529027000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0547
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15425
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.150
_diffrn_reflns_theta_max         67.150
_diffrn_reflns_theta_min         4.417
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.709
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88835
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       plate
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.00162(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     508
_refine_ls_number_reflns         6779
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0565
_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^)+(0.0740P)^2^+0.0111P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1447
_refine_ls_wR_factor_ref         0.1779
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4196
_reflns_number_total             6779
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc02399c2.cif
_cod_data_source_block           202009191
_cod_depositor_comments
'Adding full bibliography for 7128552--7128554.cif.'
_cod_original_cell_volume        3818.6(8)
_cod_database_code               7128554
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C30H30O2N2
_chemical_oxdiff_usercomment     r
_shelx_estimated_absorpt_t_max   0.952
_shelx_estimated_absorpt_t_min   0.883
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C6(H6), C8(H8), C9(H9), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18),
 C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C6'(H6'), C8'(H8'), C9'(H9'),
  C14'(H14'), C15'(H15'), C16'(H16'), C17'(H17'), C18'(H18'), C20'(H20'),
 C21'(H21'), C22'(H22'), C23'(H23'), C24'(H24')
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C10'(H10D,H10E,H10F)
;
_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 2.856
_oxdiff_exptl_absorpt_empirical_full_min 0.788