Electrochemical and mechanochemical synthesis of dihydrofuro[3,2-c]chromenones via intramolecular Csp3–H cross-dehydrogenative oxygenation within warfarin frameworks: an efficient and straightforward dual approach
Karmakar, Indrajit; Brahmachari, Goutam; Green Chemistry 24 (2022) 2825–2838; doi:10.1039/D2GC00146B

data_7244644
_publ_section_title
;
 Electrochemical and mechanochemical synthesis of
 dihydrofuro[3,2-c]chromenones via intramolecular Csp3--H
 cross-dehydrogenative oxygenation within warfarin frameworks: an
 efficient and straightforward dual approach
;
_journal_issue                   7
_journal_name_full               'Green Chemistry'
_journal_page_first              2825
_journal_page_last               2838
_journal_paper_doi               10.1039/D2GC00146B
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C24 H16 O5'
_chemical_formula_sum            'C24 H16 O5'
_chemical_formula_weight         384.37
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-05-25
_audit_creation_method
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_audit_update_record
;
2022-01-07 deposited with the CCDC.	2022-03-01 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.275(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.9980(5)
_cell_length_b                   19.0007(14)
_cell_length_c                   18.7257(19)
_cell_measurement_reflns_used    1389
_cell_measurement_temperature    150.0(7)
_cell_measurement_theta_max      28.1490
_cell_measurement_theta_min      2.3950
_cell_volume                     1767.6(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(7)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9974
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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     37.00  90.00   1.00   20.00    --   26.84 178.00  60.00   53
  2  \w     -8.00  94.00   1.00   20.00    --   26.84  57.00-120.00  102
  3  \w     54.00 114.00   1.00   20.00    --   26.84 178.00-180.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0241768000
_diffrn_orient_matrix_UB_12      -0.0305238000
_diffrn_orient_matrix_UB_13      0.0201946000
_diffrn_orient_matrix_UB_21      0.1080583000
_diffrn_orient_matrix_UB_22      0.0091092000
_diffrn_orient_matrix_UB_23      0.0258967000
_diffrn_orient_matrix_UB_31      -0.0894568000
_diffrn_orient_matrix_UB_32      0.0194863000
_diffrn_orient_matrix_UB_33      0.0194889000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1695
_diffrn_reflns_av_unetI/netI     0.1841
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5401
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.52
_diffrn_reflns_theta_min         2.19
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59117
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       monoclinic
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.314
_exptl_crystal_size_mid          0.254
_exptl_crystal_size_min          0.156
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.934
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3658
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.934
_refine_ls_R_factor_all          0.1489
_refine_ls_R_factor_gt           0.0982
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0980P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2102
_refine_ls_wR_factor_ref         0.2541
_reflns_number_gt                1822
_reflns_number_total             3658
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2gc00146b2.cif
_cod_data_source_block           gb_1885_lt_mo
_cod_depositor_comments          'Adding full bibliography for 7244644.cif.'
_cod_database_code               7244644
_chemical_oxdiff_formula         'c h n o s'
_reflns_odcompleteness_completeness 98.40
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C11(H11)
2.b Aromatic/amide H refined with riding coordinates:
 C24(H24), C14(H14), C6(H6), C3(H3), C22(H22), C5(H5A), C20(H20), C21(H21),
 C4(H4), C23(H23), C16(H16), C15(H15), C17(H17)
2.c Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_olex2_date_sample_data_collection 2021-05-24
_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 3.926
_oxdiff_exptl_absorpt_empirical_full_min 0.618