Visible-light-mediated radical difunctionalization of alkenes with aromatic aldehydes.
Xu, Zhenhua; Geng, Tao; Du, Jun; Zuo, Youpeng; Hu, Xiaoxiao; Liu, Lin; Shi, Zhiqiang; Huang, Huawen; Organic & biomolecular chemistry 23 (2025) 2625–2629; doi:10.1039/d4ob02090a

data_7160377
_publ_section_title
;
 Visible-light-mediated radical difunctionalization of alkenes with
 aromatic aldehydes.
;
_journal_issue                   11
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2625
_journal_page_last               2629
_journal_paper_doi               10.1039/d4ob02090a
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C13 H14 O5'
_chemical_formula_sum            'C13 H14 O5'
_chemical_formula_weight         250.24
_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     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2g57nk
_audit_creation_date             2023-04-15
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2024-05-28 deposited with the CCDC.	2025-02-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 117.585(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.7949(8)
_cell_length_b                   6.9944(3)
_cell_length_c                   14.1314(8)
_cell_measurement_reflns_used    1811
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      72.8830
_cell_measurement_theta_min      6.2870
_cell_volume                     1208.50(14)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (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      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.965
_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    -53.00  -4.00   1.00    1.00    --  -40.98 125.00  30.00   49
  2  \w   -115.00 -18.00   1.00    1.00    --  -40.98 -37.00 -60.00   97
  3  \w   -113.00 -19.00   1.00    1.00    --  -40.98 -57.00-150.00   94
  4  \w     38.00 137.00   1.00    1.62    --  107.58 -61.00   0.00   99
  5  \w     98.00 125.00   1.00    1.62    --  107.58  38.00 146.00   27
  6  \w    135.00 168.00   1.00    1.62    --  107.58 125.00  30.00   33
  7  \w     87.00 164.00   1.00    1.62    --  107.58  30.00-180.00   77
  8  \w     34.00 106.00   1.00    1.62    --  107.58-125.00   0.00   72
  9  \w     49.00 136.00   1.00    1.62    --  107.58 -30.00 150.00   87
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1221506000
_diffrn_orient_matrix_UB_12      -0.0362387000
_diffrn_orient_matrix_UB_13      -0.0748333000
_diffrn_orient_matrix_UB_21      -0.0115441000
_diffrn_orient_matrix_UB_22      -0.0968961000
_diffrn_orient_matrix_UB_23      0.0922323000
_diffrn_orient_matrix_UB_31      -0.0285686000
_diffrn_orient_matrix_UB_32      0.1943953000
_diffrn_orient_matrix_UB_33      0.0319479000
_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  0.0391
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4219
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.936
_diffrn_reflns_theta_min         3.615
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.893
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39369
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.118
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2369
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0801
_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^)+(0.1413P)^2^+0.0928P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2056
_refine_ls_wR_factor_ref         0.2216
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1928
_reflns_number_total             2369
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob02090a2.cif
_cod_data_source_block           20649
_cod_depositor_comments          'Adding full bibliography for 7160377.cif.'
_cod_original_cell_volume        1208.50(13)
_cod_database_code               7160377
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C11(H11A,H11B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C4(H4), C5(H5A), C6(H6)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3), O5(H5)
;
_shelx_res_checksum              81105
_olex2_date_sample_data_collection 2023-04-13
_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 1.994
_oxdiff_exptl_absorpt_empirical_full_min 0.512