Photocatalytic synthesis of tetra-substituted furans promoted by carbon dioxide.
Tian, Ya-Ming; Wang, Huaiju; Ritu, ?; König, Burkhard; Chemical science 13 (2021) 241–246; doi:10.1039/d1sc06403g

data_1565674
_publ_section_title
;
 Photocatalytic synthesis of tetra-substituted furans promoted by carbon
 dioxide.
;
_journal_issue                   1
_journal_name_full               'Chemical science'
_journal_page_first              241
_journal_page_last               246
_journal_paper_doi               10.1039/d1sc06403g
_journal_volume                  13
_journal_year                    2021
_chemical_formula_moiety         'C20 H16 O3'
_chemical_formula_sum            'C20 H16 O3'
_chemical_formula_weight         304.33
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-01
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-10-01 deposited with the CCDC.	2021-12-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.3790(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.53430(10)
_cell_length_b                   17.21120(10)
_cell_length_c                   11.54650(10)
_cell_measurement_reflns_used    11229
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      73.1320
_cell_measurement_theta_min      3.7910
_cell_volume                     1490.69(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.976
_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     45.00 106.00   0.50    0.60    --   75.27   0.00  90.00  122
  2  \w     44.00 106.00   0.50    0.60    --   75.27   0.00 150.00  124
  3  \w     30.00  95.00   0.50    0.50    --   62.53   0.00 -30.00  130
  4  \w     46.00 106.00   0.50    0.60    --   75.27   0.00  30.00  120
  5  \w     66.00 107.00   0.50    0.60    --   75.27   0.00 -30.00   82
  6  \w     36.00 103.00   0.50    0.50    --   62.53  15.00-150.00  134
  7  \w    -92.00 -66.00   0.50    0.50    --  -68.34 125.00 -30.00   52
  8  \w    -92.00 -29.00   0.50    0.50    --  -68.34 125.00-150.00  126
  9  \w    -92.00 -29.00   0.50    0.50    --  -68.34 125.00  90.00  126
 10  \w    -92.00 -29.00   0.50    0.50    --  -68.34 125.00 150.00  126
 11  \w   -101.00 -36.00   0.50    0.50    --  -68.34   0.00  60.00  130
 12  \w    -97.00 -32.00   0.50    0.50    --  -64.39   0.00   0.00  130
 13  \w   -102.00 -42.00   0.50    0.50    --  -68.34 -15.00 -30.00  120
 14  \w   -101.00 -36.00   0.50    0.50    --  -68.34   0.00-120.00  130
 15  \w     36.00  98.00   0.50    0.60    --   75.27-125.00  30.00  124
 16  \w     24.00  86.00   0.50    0.50    --   62.53-125.00   0.00  124
 17  \w     35.00  61.00   0.50    0.50    --   72.38-125.00   0.00   52
 18  \w     36.00  99.00   0.50    0.60    --   75.27-125.00-150.00  126
 19  \w     36.00  99.00   0.50    0.60    --   75.27-125.00 -30.00  126
 20  \w     71.00  96.00   0.50    0.50    --   72.38-125.00   0.00   50
 21  \w     36.00  64.00   0.50    0.60    --   75.27-125.00  90.00   56
 22  \w     37.00  65.00   0.50    0.60    --   75.27-125.00 150.00   56
 23  \w     74.00  99.00   0.50    0.60    --   75.27-125.00 150.00   50
 24  \w     74.00  99.00   0.50    0.60    --   75.27-125.00  90.00   50
 25  \w     36.00  99.00   0.50    0.60    --   75.27-125.00 -90.00  126
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0539185000
_diffrn_orient_matrix_UB_12      0.0177427000
_diffrn_orient_matrix_UB_13      0.1227395000
_diffrn_orient_matrix_UB_21      0.0830029000
_diffrn_orient_matrix_UB_22      0.0815684000
_diffrn_orient_matrix_UB_23      -0.0053830000
_diffrn_orient_matrix_UB_31      -0.1798880000
_diffrn_orient_matrix_UB_32      0.0323433000
_diffrn_orient_matrix_UB_33      -0.0535644000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0159
_diffrn_reflns_av_unetI/netI     0.0102
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16491
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.045
_diffrn_reflns_theta_min         4.626
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.730
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.831
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_description       prism
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.127
_exptl_crystal_size_mid          0.093
_exptl_crystal_size_min          0.042
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2918
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0317
_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^)+(0.0399P)^2^+0.5646P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0813
_refine_ls_wR_factor_ref         0.0822
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2764
_reflns_number_total             2918
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc06403g2.cif
_cod_data_source_block           u020
_cod_depositor_comments          'Adding full bibliography for 1565674.cif.'
_cod_database_code               1565674
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C20 H16 O3'
_chemical_oxdiff_usercomment     Tian_Koenig_TYM-211220
_shelx_estimated_absorpt_t_max   0.970
_shelx_estimated_absorpt_t_min   0.913
_reflns_odcompleteness_completeness 99.86
_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:
 C14(H14), C7(H7), C18(H18), C15(H15), C9(H9), C17(H17), C11(H11), C10(H10),
 C8(H8), C16(H16)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C1(H1A,H1B,H1C)
;
_shelx_res_checksum              10929
_shelx_hkl_checksum              31700
_olex2_date_sample_data_collection 2021-02-25
_olex2_date_sample_submission    2021-02-22
_olex2_submission_original_sample_id TYM-211220
_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 1.209
_oxdiff_exptl_absorpt_empirical_full_min 0.861