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_1572880
_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         'C26 H20 Br N O4'
_chemical_formula_sum            'C26 H20 Br N O4'
_chemical_formula_weight         490.34
_chemical_name_systematic
2-(4-bromobenzoyel)-3-(4-dimethylamio)phenyl)-2,3-dihydro-4H-furo[3,2-c]chromen-4-one
_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     iterative
_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                82.4456(10)
_cell_angle_beta                 83.3581(12)
_cell_angle_gamma                85.9012(11)
_cell_formula_units_Z            2
_cell_length_a                   5.03990(8)
_cell_length_b                   14.26675(16)
_cell_length_c                   15.1370(2)
_cell_measurement_reflns_used    13185
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      68.2450
_cell_measurement_theta_min      2.9540
_cell_volume                     1069.96(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.58a (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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_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 0.998
_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    -26.00  43.00   0.50    0.20    --   40.33 -38.00  90.00  138
  2  \w    -26.00  57.00   0.50    0.20    --   40.33 -50.00   0.00  166
  3  \w    -35.00  24.00   0.50    0.20    --   40.33 -12.00 -60.00  118
  4  \w    -30.00  31.00   0.50    0.20    --   40.33 -25.00-180.00  122
  5  \w    -35.00  24.00   0.50    0.20    --   40.33 -12.00-150.00  118
  6  \w    -35.00  24.00   0.50    0.20    --   40.33 -12.00-120.00  118
  7  \w     12.00  43.00   0.50    0.20    --   40.33  81.00 122.65   62
  8  \w      9.00  43.00   0.50    0.20    --   40.33  90.00 170.73   68
  9  \w     14.00 109.00   0.50    0.20    --   40.33  77.00  60.00  190
 10  \w     14.00 109.00   0.50    0.20    --   40.33  77.00 150.00  190
 11  \w     14.00 109.00   0.50    0.20    --   40.33  77.00   0.00  190
 12  \w     14.00 109.00   0.50    0.20    --   40.33  77.00 -90.00  190
 13  \w     11.00  43.00   0.50    0.20    --   40.33  85.00 -48.43   64
 14  \w     83.00 164.00   0.50    0.20    --   96.67  33.00-180.00  162
 15  \w     78.00 163.00   0.50    0.20    --   96.67  50.00-150.00  170
 16  \w     78.00 163.00   0.50    0.20    --   96.67  50.00 -30.00  170
 17  \w     75.00 164.00   0.50    0.20    --   96.67  59.00  30.00  178
 18  \w     78.00 163.00   0.50    0.20    --   96.67  50.00  90.00  170
 19  \w     73.00 165.00   0.50    0.20    --   96.67  68.00 120.00  184
 20  \w     74.00 162.00   0.50    0.20    --   96.67 155.00  19.00  176
 21  \w    105.00 170.00   0.50    0.20    --   96.67  96.00 -90.00  130
 22  \w     97.00 163.00   0.50    0.20    --   96.67 121.00-138.00  132
 23  \w     81.00 164.00   0.50    0.20    --   96.67 145.00-180.00  166
 24  \w     99.00 164.00   0.50    0.20    --   96.67 117.00-150.00  130
 25  \w     30.00  57.00   0.50    0.20    --   96.67 -50.00-120.00   54
 26  \w     29.00  68.00   0.50    0.20    --   96.67 -59.00-180.00   78
 27  \w     29.00  83.00   0.50    0.20    --   96.67 -68.00-150.00  108
 28  \w     28.00 105.00   0.50    0.20    --   96.67 -77.00 -30.00  154
 29  \w     29.00  68.00   0.50    0.20    --   96.67 -59.00  30.00   78
 30  \w     29.00  83.00   0.50    0.20    --   96.67 -68.00 150.00  108
 31  \w     27.00 127.00   0.50    0.20    --   96.67 -87.00 120.00  200
 32  \w     31.00 111.00   0.50    0.20    --   96.67-121.00 138.00  160
 33  \w     44.00 127.00   0.50    0.20    --   96.67-145.00  60.00  166
 34  \w     30.00 109.00   0.50    0.20    --   96.67-117.00  60.00  158
 35  \w     49.00 133.00   0.50    0.20    --   96.67-155.00 -18.00  168
 36  \w     30.00 109.00   0.50    0.20    --   96.67-117.00 -30.00  158
 37  \w     44.00 127.00   0.50    0.20    --   96.67-145.00 -60.00  166
 38  \w     22.00 106.00   0.50    0.20    --   96.67 -96.00 -30.00  168
 39  \w     30.00 109.00   0.50    0.20    --   96.67-117.00-150.00  158
 40  \w     49.00 110.00   0.50    0.20    --   40.33-155.00 -18.00  122
 41  \w     31.00  88.00   0.50    0.20    --   40.33-121.00 138.00  114
 42  \w   -110.00 -26.00   0.50    0.20    --  -40.33 -25.00 -60.00  168
 43  \w   -108.00 -17.00   0.50    0.20    --  -40.33 -64.00-150.00  182
 44  \w   -107.00 -21.00   0.50    0.20    --  -40.33 -50.00 -90.00  172
 45  \w   -106.00 -25.00   0.50    0.20    --  -40.33 -38.00-150.00  162
 46  \w   -107.00 -21.00   0.50    0.20    --  -40.33 -50.00   0.00  172
 47  \w   -108.00 -17.00   0.50    0.20    --  -40.33 -64.00 150.00  182
 48  \w   -108.00 -17.00   0.50    0.20    --  -40.33 -64.00  90.00  182
 49  \w   -109.00 -52.00   0.50    0.20    --  -40.33-155.00 -18.00  114
 50  \w   -146.00 -52.00   0.50    0.20    --  -82.50-155.00 -18.00  188
 51  \w   -149.00 -75.00   0.50    0.20    --  -82.50-121.00 138.00  148
 52  \w   -153.00 -78.00   0.50    0.20    --  -82.50 -87.00  30.00  150
 53  \w   -156.00 -58.00   0.50    0.20    --  -82.50 -17.00-120.00  196
 54  \w    -83.00 -14.00   0.50    0.20    --  -82.50  68.00  60.00  138
 55  \w    -47.00 -15.00   0.50    0.20    --  -82.50  42.00  90.00   64
 56  \w   -107.00 -27.00   0.50    0.20    --  -40.33 155.00  19.00  160
 57  \w    -85.00  -9.00   0.50    0.20    --  -40.33 121.00-138.00  152
 58  \w    -84.00 -15.00   0.50    0.20    --  -82.50 121.00-138.00  138
 59  \w    -47.00 -15.00   0.50    0.20    --  -82.50  42.00 -90.00   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      -0.0201922000
_diffrn_orient_matrix_UB_12      -0.0255323000
_diffrn_orient_matrix_UB_13      0.1025627000
_diffrn_orient_matrix_UB_21      0.2833392000
_diffrn_orient_matrix_UB_22      0.0338606000
_diffrn_orient_matrix_UB_23      0.0003083000
_diffrn_orient_matrix_UB_31      -0.1196839000
_diffrn_orient_matrix_UB_32      0.1005275000
_diffrn_orient_matrix_UB_33      0.0120087000
_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  0.0579
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16451
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.182
_diffrn_reflns_theta_min         2.962
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.905
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.58a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_description       block
_exptl_crystal_F_000             500
_exptl_crystal_preparation       'crystallisation done in chloroform'
_exptl_crystal_recrystallization_method 'kept in the chloroform solution'
_exptl_crystal_size_max          0.002
_exptl_crystal_size_mid          0.001
_exptl_crystal_size_min          0.001
_refine_diff_density_max         0.583
_refine_diff_density_min         -0.834
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       0.0026(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         3872
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0394
_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^)+(0.0686P)^2^+0.5955P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1069
_refine_ls_wR_factor_ref         0.1079
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3682
_reflns_number_total             3872
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc04720f2.cif
_cod_data_source_block           ksk_kc_65_auto
_cod_depositor_comments
'Adding full bibliography for 1572879--1572880.cif.'
_cod_database_code               1572880
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O Br'
_chemical_oxdiff_usercomment     100K
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.994
_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 Ternary CH refined with riding coordinates:
 C2(H2), C1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C27(H27), C18(H18), C6(H6), C28(H28), C31(H31), C16(H16), C15(H15),
 C30(H30), C9(H9), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              11369
_shelx_hkl_checksum              38655
_olex2_exptl_crystal_mounting_method yes
_olex2_submission_original_sample_id SD100165
_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 2.130
_oxdiff_exptl_absorpt_empirical_full_min 0.533