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_7128553
_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         'C17 H10 O4'
_chemical_formula_sum            'C17 H10 O4'
_chemical_formula_weight         278.25
_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     direct
_audit_creation_date             2020-10-09
_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                94.814(11)
_cell_angle_beta                 90.307(13)
_cell_angle_gamma                112.254(14)
_cell_formula_units_Z            2
_cell_length_a                   7.1288(11)
_cell_length_b                   7.3017(9)
_cell_length_c                   13.738(2)
_cell_measurement_reflns_used    807
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.1750
_cell_measurement_theta_min      6.4440
_cell_volume                     658.96(18)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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   -102.00 -15.00   1.00    1.00    --  -33.50 -57.00  90.00   87
  2  \w     57.00 111.00   1.00    1.00    --   36.62 178.00  90.00   54
  3  \w    -35.00 108.00   1.00    1.00    --   36.62   0.00  90.00  143
  4  \w     57.00 111.00   1.00    1.00    --   36.62 178.00 -30.00   54
  5  \w     -4.00  77.00   1.00    1.00    --   36.62 -99.00 -90.00   81
  6  \w     -4.00  77.00   1.00    1.00    --   36.62 -99.00  30.00   81
  7  \w     14.00 107.00   1.00    1.00    --   36.62  37.00  90.00   93
  8  \w     57.00 111.00   1.00    1.00    --   36.62 178.00 -90.00   54
  9  \w     -4.00  77.00   1.00    1.00    --   36.62 -99.00  90.00   81
 10  \w    -32.00  55.00   1.00    1.00    --   36.62 -57.00 120.00   87
 11  \w     14.00 107.00   1.00    1.00    --   36.62  37.00 -30.00   93
 12  \w    106.00 154.00   1.00    3.00    --  108.00 111.00 -60.00   48
 13  \w     79.00 110.00   1.00    3.00    --  108.00-111.00-120.00   31
 14  \w     48.00 122.00   1.00    3.00    --  108.00 -61.00 150.00   74
 15  \w    119.00 165.00   1.00    3.00    --  108.00 111.00 150.00   46
 16  \w     47.00 109.00   1.00    3.00    --  108.00 -94.00 120.00   62
 17  \w    116.00 150.00   1.00    3.00    --  108.00 178.00-180.00   34
 18  \w    114.00 146.00   1.00    3.00    --  108.00 111.00 -90.00   32
 19  \w    143.00 174.00   1.00    3.00    --  108.00  61.00   0.00   31
 20  \w     94.00 121.00   1.00    3.00    --  108.00  61.00   0.00   27
 21  \w     70.00  98.00   1.00    3.00    --  108.00 178.00-180.00   28
 22  \w     43.00 114.00   1.00    3.00    --  108.00 -45.00   0.00   71
 23  \w     73.00 103.00   1.00    3.00    --  108.00-111.00   0.00   30
 24  \w    102.00 127.00   1.00    3.00    --  108.00 111.00  60.00   25
 25  \w    147.00 176.00   1.00    3.00    --  108.00 111.00  60.00   29
 26  \w     38.00  65.00   1.00    3.00    --  108.00-111.00   0.00   27
 27  \w     39.00 148.00   1.00    3.00    --  108.00 -15.00-180.00  109
 28  \w     50.00 128.00   1.00    3.00    --  108.00 -61.00-120.00   78
 29  \w     90.00 176.00   1.00    3.00    --  108.00  30.00-150.00   86
;
_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      -0.0601985000
_diffrn_orient_matrix_UB_12      -0.1479047000
_diffrn_orient_matrix_UB_13      0.0788248000
_diffrn_orient_matrix_UB_21      0.1455523000
_diffrn_orient_matrix_UB_22      0.1605645000
_diffrn_orient_matrix_UB_23      0.0748512000
_diffrn_orient_matrix_UB_31      -0.1726269000
_diffrn_orient_matrix_UB_32      0.0690217000
_diffrn_orient_matrix_UB_33      0.0294833000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4663
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.059
_diffrn_reflns_theta_max         67.059
_diffrn_reflns_theta_min         6.472
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.835
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85387
_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            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_description       octahedral
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2352
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0994
_refine_ls_R_factor_gt           0.0638
_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^)+(0.1090P)^2^+0.0550P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1804
_refine_ls_wR_factor_ref         0.2205
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1404
_reflns_number_total             2352
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc02399c2.cif
_cod_data_source_block           202010208
_cod_depositor_comments
'Adding full bibliography for 7128552--7128554.cif.'
_cod_original_cell_volume        658.95(18)
_cod_database_code               7128553
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C30H3O3N4
_chemical_oxdiff_usercomment     r
_shelx_estimated_absorpt_t_max   0.967
_shelx_estimated_absorpt_t_min   0.838
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17)
;
_shelx_res_checksum              9804
_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 1.397
_oxdiff_exptl_absorpt_empirical_full_min 0.609