Stepwise benzylic oxygenation via uranyl-photocatalysis
Hu, Deqing; Jiang, Xuefeng; Green Chemistry 24 (2022) 124–129; doi:10.1039/D1GC04042A

data_7244048
_publ_section_title
;
 Stepwise benzylic oxygenation via uranyl-photocatalysis
;
_journal_issue                   1
_journal_name_full               'Green Chemistry'
_journal_page_first              124
_journal_page_last               129
_journal_paper_doi               10.1039/D1GC04042A
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C12 H14 O3'
_chemical_formula_sum            'C12 H14 O3'
_chemical_formula_weight         206.23
_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_creation_date             2019-01-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-11-01 deposited with the CCDC.	2021-12-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.867(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.7291(6)
_cell_length_b                   7.5614(2)
_cell_length_c                   8.1518(2)
_cell_measurement_reflns_used    9256
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.1980
_cell_measurement_theta_min      5.0940
_cell_volume                     1065.36(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.989
_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    -35.00  15.00   1.00    2.00    --    0.00 -29.00 -52.00   50
  2  \w      5.00  30.00   1.00    2.00    --    0.00  29.00 109.00   25
  3  \w     76.00 185.00   1.00    2.00    --   95.80  29.00 109.00  109
  4  \w     60.00  98.00   1.00    2.00    --   95.80 -29.00 -52.00   38
  5  \w     27.00  53.00   1.00    2.00    --    0.00  19.00 -60.00   26
  6  \w    -23.00  25.00   1.00    2.00    --    0.00  19.00  30.00   48
  7  \w     46.00  84.00   1.00    2.00    --    0.00  57.00 150.00   38
  8  \w    -28.00  88.00   1.00    2.00    --    0.00  77.00-180.00  116
  9  \w    -89.00 -56.00   1.00    2.00    --    0.00 -38.00-180.00   33
 10  \w    -21.00  54.00   1.00    2.00    --    0.00  57.00  60.00   75
 11  \w     43.00  85.00   1.00    2.00    --    0.00  57.00 -60.00   42
 12  \w     63.00  88.00   1.00    2.00    --    0.00  38.00 -90.00   25
 13  \w     10.00  56.00   1.00    2.00    --    0.00  38.00 -90.00   46
 14  \w     45.00  71.00   1.00    2.00    --    0.00  29.00 109.00   26
 15  \w    -24.00   4.00   1.00    2.00    --    0.00  19.00 -60.00   28
 16  \w     -1.00  25.00   1.00    2.00    --    0.00  57.00 -60.00   26
 17  \w    -21.00  41.00   1.00    2.00    --    0.00  57.00 150.00   62
 18  \w    -31.00  16.00   1.00    2.00    --    0.00 -38.00-180.00   47
 19  \w    155.00 181.00   1.00    2.00    --   95.80  80.00  76.30   26
 20  \w    104.00 130.00   1.00    2.00    --   95.80  80.00  76.30   26
 21  \w     75.00 184.00   1.00    2.00    --   95.80  45.00  60.00  109
 22  \w     66.00  92.00   1.00    2.00    --   95.80  80.00  76.30   26
 23  \w     64.00  90.00   1.00    2.00    --   95.80  82.00 120.00   26
 24  \w     67.00 125.00   1.00    2.00    --   95.80 -82.00  90.00   58
 25  \w     10.00  68.00   1.00    2.00    --   95.80 -82.00 -90.00   58
 26  \w      6.00 127.00   1.00    2.00    --   95.80 -82.00  60.00  121
 27  \w     71.00 130.00   1.00    2.00    --   95.80  61.00-105.87   59
 28  \w     65.00  91.00   1.00    2.00    --   95.80  77.00 -60.00   26
 29  \w     65.00  90.00   1.00    2.00    --   95.80  77.00-150.00   25
 30  \w     63.00 184.00   1.00    2.00    --   95.80  82.00 138.89  121
 31  \w     67.00  92.00   1.00    2.00    --   95.80  74.00 -29.91   25
 32  \w     69.00 126.00   1.00    2.00    --   95.80 -82.00 -30.00   57
 33  \w     68.00 137.00   1.00    2.00    --   95.80  70.00 125.90   69
 34  \w    142.00 177.00   1.00    2.00    --   95.80  70.00 125.90   35
 35  \w     93.00 125.00   1.00    2.00    --   95.80 -77.00-150.00   32
 36  \w     63.00 185.00   1.00    2.00    --   95.80  82.00 -30.00  122
 37  \w     14.00  87.00   1.00    2.00    --   95.80 -77.00-150.00   73
 38  \w     64.00  90.00   1.00    2.00    --   95.80  80.00 101.72   26
 39  \w     63.00  98.00   1.00    2.00    --   95.80  82.00  30.00   35
 40  \w     12.00  57.00   1.00    2.00    --   95.80 -82.00  90.00   45
 41  \w     65.00  90.00   1.00    2.00    --   95.80  77.00  90.00   25
 42  \w     68.00  94.00   1.00    2.00    --   95.80  74.00 -44.02   26
 43  \w    140.00 169.00   1.00    2.00    --   95.80  45.00 -30.00   29
 44  \w     75.00 141.00   1.00    2.00    --   95.80  61.00  30.00   66
 45  \w    158.00 183.00   1.00    2.00    --   95.80  61.00  30.00   25
 46  \w     71.00  97.00   1.00    2.00    --   95.80  61.00  90.00   26
 47  \w    146.00 172.00   1.00    2.00    --   95.80  61.00  90.00   26
 48  \w     65.00  90.00   1.00    2.00    --   95.80  77.00  30.00   25
 49  \w     65.00 130.00   1.00    2.00    --   95.80  76.00   0.00   65
 50  \w     75.00 152.00   1.00    2.00    --   95.80  45.00-120.00   77
 51  \w     64.00  90.00   1.00    2.00    --   95.80  82.00-150.00   26
 52  \w    140.00 176.00   1.00    2.00    --   95.80  61.00-105.87   36
 53  \w    135.00 182.00   1.00    2.00    --   95.80  82.00 -83.62   47
 54  \w     64.00  90.00   1.00    2.00    --   95.80  82.00  90.00   26
 55  \w     75.00 118.00   1.00    2.00    --   95.80  45.00 -30.00   43
 56  \w     64.00  90.00   1.00    2.00    --   95.80  82.00 -83.62   26
 57  \w     12.00 122.00   1.00    2.00    --   95.80 -82.00-180.00  110
 58  \w     66.00  92.00   1.00    2.00    --   95.80  77.00  60.00   26
 59  \w     65.00 156.00   1.00    2.00    --   95.80  77.00 -90.00   91
 60  \w     66.00  91.00   1.00    2.00    --   95.80  74.00 176.21   25
 61  \w     63.00 129.00   1.00    2.00    --   95.80  82.00-180.00   66
 62  \w     77.00 124.00   1.00    2.00    --   95.80 -82.00 -90.00   47
 63  \w     71.00  97.00   1.00    2.00    --   95.80  61.00-180.00   26
 64  \w     63.00  88.00   1.00    2.00    --   95.80  82.00-120.00   25
 65  \w     63.00  89.00   1.00    2.00    --   95.80  82.00   0.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0289235000
_diffrn_orient_matrix_UB_12      0.0058966000
_diffrn_orient_matrix_UB_13      0.1926488000
_diffrn_orient_matrix_UB_21      0.0153538000
_diffrn_orient_matrix_UB_22      0.1998463000
_diffrn_orient_matrix_UB_23      -0.0094283000
_diffrn_orient_matrix_UB_31      -0.0829276000
_diffrn_orient_matrix_UB_32      0.0390657000
_diffrn_orient_matrix_UB_33      0.0190480000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1087
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            23666
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.334
_diffrn_reflns_theta_min         5.118
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.751
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.01640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
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    1.286
_exptl_crystal_description       plate
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.021(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2147
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0499
_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^)+(0.0873P)^2^+0.1134P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1432
_refine_ls_wR_factor_ref         0.1488
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1824
_reflns_number_total             2147
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1gc04042a2.cif
_cod_data_source_block           exp_628
_cod_depositor_comments          'Adding full bibliography for 7244048.cif.'
_cod_database_code               7244048
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.915
_shelx_estimated_absorpt_t_min   0.714
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C6(H6), C5(H5)
2.d Tetrahedral OH refined with riding coordinates:
 O2(H2)
;
_shelx_res_checksum              32544
_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 40.965
_oxdiff_exptl_absorpt_empirical_full_min 0.225