Solvent-promoted photochemical carbonylation of benzylic C-H bonds under iron catalysis.
Qi, Rui; Bai, Tianwen; Tang, Shuwang; Hou, Ming; Zhang, Zhide; Xie, Wenlin; Deng, Yangling; Zhou, Hongwei; Qiu, Guanyinsheng; Organic & biomolecular chemistry 21 (2023) 5382–5386; doi:10.1039/d3ob00328k

data_7159450
_publ_section_title
;
 Solvent-promoted photochemical carbonylation of benzylic C-H bonds under
 iron catalysis.
;
_journal_issue                   26
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5382
_journal_page_last               5386
_journal_paper_doi               10.1039/d3ob00328k
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C14 H9 O'
_chemical_formula_sum            'C14 H9 O'
_chemical_formula_weight         193.21
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-11-28
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2022-12-09 deposited with the CCDC.	2023-06-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.970(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.8930(10)
_cell_length_b                   7.7491(4)
_cell_length_c                   13.6613(7)
_cell_measurement_reflns_used    1294
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.2400
_cell_measurement_theta_min      4.0480
_cell_volume                     1893.93(17)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0802
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.978
_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     79.00 109.00   1.00    1.00    --   36.33 178.00  30.00   30
  2  \w     43.00  69.00   1.00    1.00    --   36.33 -99.00 -30.00   26
  3  \w     12.00  41.00   1.00    1.00    --   36.33  77.00 150.00   29
  4  \w     -1.00  25.00   1.00    1.00    --   36.33 -99.00 -30.00   26
  5  \w     54.00 103.00   1.00    1.00    --   36.33  77.00-150.00   49
  6  \w     12.00  49.00   1.00    1.00    --   36.33  77.00-150.00   37
  7  \w     58.00 109.00   1.00    1.00    --   36.33 178.00  90.00   51
  8  \w     63.00  89.00   1.00    1.00    --   36.33-178.00-150.00   26
  9  \w     65.00 100.00   1.00    1.00    --   36.33  77.00 150.00   35
 10  \w     62.00 113.00   1.00    2.38    --  108.00-111.00 -30.00   51
 11  \w     49.00 124.00   1.00    2.38    --  108.00 -61.00-180.00   75
 12  \w     45.00  88.00   1.00    2.38    --  108.00 -77.00  90.00   43
 13  \w     83.00 123.00   1.00    2.38    --  108.00 -45.00  30.00   40
 14  \w     43.00  68.00   1.00    2.38    --  108.00 -45.00  30.00   25
 15  \w     44.00 107.00   1.00    2.38    --  108.00 -95.00-180.00   63
 16  \w     94.00 165.00   1.00    2.38    --  108.00  45.00   0.00   71
 17  \w     94.00 136.00   1.00    2.38    --  108.00  61.00 -60.00   42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0840837000
_diffrn_orient_matrix_UB_12      -0.0059262000
_diffrn_orient_matrix_UB_13      0.0262532000
_diffrn_orient_matrix_UB_21      -0.0168607000
_diffrn_orient_matrix_UB_22      -0.1122538000
_diffrn_orient_matrix_UB_23      0.0900515000
_diffrn_orient_matrix_UB_31      0.0085461000
_diffrn_orient_matrix_UB_32      -0.1637907000
_diffrn_orient_matrix_UB_33      -0.0626065000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3062
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.830
_diffrn_reflns_theta_min         4.944
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.663
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40357
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.680
_refine_diff_density_rms         0.203
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1819
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0670
_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^)+(0.1063P)^2^+0.1837P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1604
_refine_ls_wR_factor_ref         0.1731
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1511
_reflns_number_total             1819
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00328k2.cif
_cod_data_source_block           20220623-1
_cod_database_code               7159450
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C H O N'
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C002(H002)
2.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C008(H008), C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D),
 C00E(H00E), C00F(H00F)
;
_shelx_res_checksum              57094
_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 2.975
_oxdiff_exptl_absorpt_empirical_full_min 0.643