Electron donor-acceptor complex enabled photocascade strategy for the synthesis of <i>trans</i>-dihydrofuro[3,2-<i>c</i>]chromen-4-one scaffolds <i>via</i> radical conjugate addition of pyridinium ylide.
Dey, Sovan; Das, Arindam; Yadav, Ram Naresh; Boruah, Palash Jyoti; Sarkar, Koushik; Paul, Amit Kumar; Hossain, Md Firoj; Chemical communications (Cambridge, England) 60 (2024) 14384–14387; doi:10.1039/d4cc04720f

data_1572879
_publ_section_title
;
 Electron donor-acceptor complex enabled photocascade strategy for the
 synthesis of <i>trans</i>-dihydrofuro[3,2-<i>c</i>]chromen-4-one
 scaffolds <i>via</i> radical conjugate addition of pyridinium ylide.
;
_journal_issue                   97
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              14384
_journal_page_last               14387
_journal_paper_doi               10.1039/d4cc04720f
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C24 H15 Cl O4'
_chemical_formula_sum            'C24 H15 Cl O4'
_chemical_formula_weight         402.81
_chemical_name_systematic
2-benzoyel-3-(2-chlorophenyl)-2,3-dihydro-4H-furo[3,2-c]chromen-4-one
_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             2023-04-15
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-07-01 deposited with the CCDC.	2024-10-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.214(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9410(4)
_cell_length_b                   8.3910(3)
_cell_length_c                   19.4783(7)
_cell_measurement_reflns_used    13645
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      27.0170
_cell_measurement_theta_min      2.1810
_cell_volume                     1864.24(12)
_computing_cell_refinement       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.957
_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     -6.00  63.00   0.50    1.71    --   12.17  39.00-144.00  138
  2  \w    -16.00  22.00   0.50    1.71    --   12.17 -57.00   0.00   76
  3  \w    -47.00 -22.00   0.50    1.71    --   12.17 -57.00   0.00   50
  4  \w    -56.00 -14.00   0.50    1.71    --   12.17 -57.00  30.00   84
  5  \w      6.00  35.00   0.50    1.71    --   12.17 -57.00  30.00   58
  6  \w     -5.00  22.00   0.50    1.71    --   12.17 -38.00  30.00   54
  7  \w    -20.00   5.00   0.50    1.71    --   12.17 -19.00   0.00   50
  8  \w    -48.00   5.00   0.50    1.71    --   12.17 -19.00 -90.00  106
  9  \w    -57.00 -32.00   0.50    1.71    --   12.17 -19.00   0.00   50
 10  \w    -45.00 -11.00   0.50    1.71    --   12.17 -38.00  30.00   68
 11  \w    -48.00 -23.00   0.50    1.71    --   12.17 -39.00  60.00   50
 12  \w    -66.00  -8.00   0.50    1.71    --  -12.01 -39.00  60.00  116
 13  \w    -21.00  16.00   0.50    1.71    --  -12.01 -99.00 150.00   74
 14  \w    -19.00  17.00   0.50    1.71    --  -12.01 -99.00  60.00   72
 15  \w    -22.00  18.00   0.50    1.71    --  -12.01 -99.00 -30.00   80
 16  \w    -13.00  18.00   0.50    1.71    --  -12.01 -99.00   0.00   62
 17  \w    -20.00   5.00   0.50    1.71    --  -12.01 -99.00 -90.00   50
 18  \w    -10.00  23.00   0.50    1.71    --  -12.01 -99.00-150.00   66
 19  \w     16.00  41.00   0.50    1.71    --   12.17 -99.00-180.00   50
 20  \w    -16.00   9.00   0.50    1.71    --   12.17 -99.00-180.00   50
 21  \w     -8.00  30.00   0.50    1.71    --   12.17 -99.00 -90.00   76
 22  \w    -38.00  12.00   0.50    1.71    --  -12.01  19.00-180.00  100
 23  \w     16.00  55.00   0.50    1.71    --  -12.01  39.00-144.00   78
 24  \w     27.00  59.00   0.50    1.71    --  -12.01  19.00-180.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0568293000
_diffrn_orient_matrix_UB_12      -0.0302589000
_diffrn_orient_matrix_UB_13      -0.0173056000
_diffrn_orient_matrix_UB_21      0.0040860000
_diffrn_orient_matrix_UB_22      0.0281969000
_diffrn_orient_matrix_UB_23      -0.0335141000
_diffrn_orient_matrix_UB_31      0.0249416000
_diffrn_orient_matrix_UB_32      -0.0736703000
_diffrn_orient_matrix_UB_33      -0.0057036000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0939
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            23819
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.091
_diffrn_reflns_theta_min         2.189
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73202
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_preparation
'crystallisation done ethylacetate in diffution of petrolium ethar'
_exptl_crystal_recrystallization_method 'in ethylacetate and petrolium ethar'
_exptl_crystal_size_max          0.002
_exptl_crystal_size_mid          0.001
_exptl_crystal_size_min          0.001
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3939
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0437
_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^)+(0.0555P)^2^+0.6718P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1189
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3328
_reflns_number_total             3939
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc04720f2.cif
_cod_data_source_block           ksk_sd_2017_auto
_cod_depositor_comments
'Adding full bibliography for 1572879--1572880.cif.'
_cod_database_code               1572879
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O'
_chemical_oxdiff_usercomment     '100 K'
_shelx_estimated_absorpt_t_max   1.000
_shelx_estimated_absorpt_t_min   1.000
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C00C(H00C), C00H(H00H)
2.b Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00F(H00F), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M),
 C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S),
 C00T(H00T)
;
_shelx_res_checksum              6634
_shelx_hkl_checksum              53221
_olex2_exptl_crystal_mounting_method yes
_olex2_submission_original_sample_id SD002017
_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 1.226
_oxdiff_exptl_absorpt_empirical_full_min 0.660