#------------------------------------------------------------------------------
#$Date: 2022-02-04 20:50:47 +0100 (vie 04 de feb de 2022) $
#$Revision: 272702 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/40/7244048.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7244048
loop_
_publ_author_name
'Hu, Deqing'
'Jiang, Xuefeng'
_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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -35.00  15.00   1.00    2.00    --    0.00 -29.00 -52.00   50
  2  ω      5.00  30.00   1.00    2.00    --    0.00  29.00 109.00   25
  3  ω     76.00 185.00   1.00    2.00    --   95.80  29.00 109.00  109
  4  ω     60.00  98.00   1.00    2.00    --   95.80 -29.00 -52.00   38
  5  ω     27.00  53.00   1.00    2.00    --    0.00  19.00 -60.00   26
  6  ω    -23.00  25.00   1.00    2.00    --    0.00  19.00  30.00   48
  7  ω     46.00  84.00   1.00    2.00    --    0.00  57.00 150.00   38
  8  ω    -28.00  88.00   1.00    2.00    --    0.00  77.00-180.00  116
  9  ω    -89.00 -56.00   1.00    2.00    --    0.00 -38.00-180.00   33
 10  ω    -21.00  54.00   1.00    2.00    --    0.00  57.00  60.00   75
 11  ω     43.00  85.00   1.00    2.00    --    0.00  57.00 -60.00   42
 12  ω     63.00  88.00   1.00    2.00    --    0.00  38.00 -90.00   25
 13  ω     10.00  56.00   1.00    2.00    --    0.00  38.00 -90.00   46
 14  ω     45.00  71.00   1.00    2.00    --    0.00  29.00 109.00   26
 15  ω    -24.00   4.00   1.00    2.00    --    0.00  19.00 -60.00   28
 16  ω     -1.00  25.00   1.00    2.00    --    0.00  57.00 -60.00   26
 17  ω    -21.00  41.00   1.00    2.00    --    0.00  57.00 150.00   62
 18  ω    -31.00  16.00   1.00    2.00    --    0.00 -38.00-180.00   47
 19  ω    155.00 181.00   1.00    2.00    --   95.80  80.00  76.30   26
 20  ω    104.00 130.00   1.00    2.00    --   95.80  80.00  76.30   26
 21  ω     75.00 184.00   1.00    2.00    --   95.80  45.00  60.00  109
 22  ω     66.00  92.00   1.00    2.00    --   95.80  80.00  76.30   26
 23  ω     64.00  90.00   1.00    2.00    --   95.80  82.00 120.00   26
 24  ω     67.00 125.00   1.00    2.00    --   95.80 -82.00  90.00   58
 25  ω     10.00  68.00   1.00    2.00    --   95.80 -82.00 -90.00   58
 26  ω      6.00 127.00   1.00    2.00    --   95.80 -82.00  60.00  121
 27  ω     71.00 130.00   1.00    2.00    --   95.80  61.00-105.87   59
 28  ω     65.00  91.00   1.00    2.00    --   95.80  77.00 -60.00   26
 29  ω     65.00  90.00   1.00    2.00    --   95.80  77.00-150.00   25
 30  ω     63.00 184.00   1.00    2.00    --   95.80  82.00 138.89  121
 31  ω     67.00  92.00   1.00    2.00    --   95.80  74.00 -29.91   25
 32  ω     69.00 126.00   1.00    2.00    --   95.80 -82.00 -30.00   57
 33  ω     68.00 137.00   1.00    2.00    --   95.80  70.00 125.90   69
 34  ω    142.00 177.00   1.00    2.00    --   95.80  70.00 125.90   35
 35  ω     93.00 125.00   1.00    2.00    --   95.80 -77.00-150.00   32
 36  ω     63.00 185.00   1.00    2.00    --   95.80  82.00 -30.00  122
 37  ω     14.00  87.00   1.00    2.00    --   95.80 -77.00-150.00   73
 38  ω     64.00  90.00   1.00    2.00    --   95.80  80.00 101.72   26
 39  ω     63.00  98.00   1.00    2.00    --   95.80  82.00  30.00   35
 40  ω     12.00  57.00   1.00    2.00    --   95.80 -82.00  90.00   45
 41  ω     65.00  90.00   1.00    2.00    --   95.80  77.00  90.00   25
 42  ω     68.00  94.00   1.00    2.00    --   95.80  74.00 -44.02   26
 43  ω    140.00 169.00   1.00    2.00    --   95.80  45.00 -30.00   29
 44  ω     75.00 141.00   1.00    2.00    --   95.80  61.00  30.00   66
 45  ω    158.00 183.00   1.00    2.00    --   95.80  61.00  30.00   25
 46  ω     71.00  97.00   1.00    2.00    --   95.80  61.00  90.00   26
 47  ω    146.00 172.00   1.00    2.00    --   95.80  61.00  90.00   26
 48  ω     65.00  90.00   1.00    2.00    --   95.80  77.00  30.00   25
 49  ω     65.00 130.00   1.00    2.00    --   95.80  76.00   0.00   65
 50  ω     75.00 152.00   1.00    2.00    --   95.80  45.00-120.00   77
 51  ω     64.00  90.00   1.00    2.00    --   95.80  82.00-150.00   26
 52  ω    140.00 176.00   1.00    2.00    --   95.80  61.00-105.87   36
 53  ω    135.00 182.00   1.00    2.00    --   95.80  82.00 -83.62   47
 54  ω     64.00  90.00   1.00    2.00    --   95.80  82.00  90.00   26
 55  ω     75.00 118.00   1.00    2.00    --   95.80  45.00 -30.00   43
 56  ω     64.00  90.00   1.00    2.00    --   95.80  82.00 -83.62   26
 57  ω     12.00 122.00   1.00    2.00    --   95.80 -82.00-180.00  110
 58  ω     66.00  92.00   1.00    2.00    --   95.80  77.00  60.00   26
 59  ω     65.00 156.00   1.00    2.00    --   95.80  77.00 -90.00   91
 60  ω     66.00  91.00   1.00    2.00    --   95.80  74.00 176.21   25
 61  ω     63.00 129.00   1.00    2.00    --   95.80  82.00-180.00   66
 62  ω     77.00 124.00   1.00    2.00    --   95.80 -82.00 -90.00   47
 63  ω     71.00  97.00   1.00    2.00    --   95.80  61.00-180.00   26
 64  ω     63.00  88.00   1.00    2.00    --   95.80  82.00-120.00   25
 65  ω     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       'ω 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+0.001xFc²λ³/sin(2θ)]^-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/[σ²(Fo²)+(0.0873P)²+0.1134P] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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)
;
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.21268(6) 0.50182(13) 0.55433(12) 0.0484(3) Uani 1 1 d . . . . .
O2 O 0.40777(7) 0.42466(18) 0.00031(14) 0.0655(4) Uani 1 1 d . . . . .
H2 H 0.442850 0.433135 -0.049950 0.098 Uiso 1 1 calc R . . . .
O3 O 0.49355(7) 0.56914(19) 0.19555(14) 0.0690(4) Uani 1 1 d . . . . .
C1 C 0.26847(8) 0.50144(17) 0.46409(16) 0.0412(3) Uani 1 1 d . . . . .
C2 C 0.24713(9) 0.42853(18) 0.30356(18) 0.0466(4) Uani 1 1 d . . . . .
H2A H 0.197611 0.382885 0.265446 0.056 Uiso 1 1 calc R . . . .
C3 C 0.29940(9) 0.42395(18) 0.20100(17) 0.0468(4) Uani 1 1 d . . . . .
H3 H 0.285071 0.373814 0.094415 0.056 Uiso 1 1 calc R . . . .
C4 C 0.37345(8) 0.49382(18) 0.25579(17) 0.0434(4) Uani 1 1 d . . . . .
C6 C 0.34304(9) 0.5678(2) 0.52182(17) 0.0475(4) Uani 1 1 d . . . . .
H6 H 0.358165 0.613335 0.630173 0.057 Uiso 1 1 calc R . . . .
C5 C 0.39425(9) 0.5654(2) 0.41650(18) 0.0481(4) Uani 1 1 d . . . . .
H5 H 0.443536 0.612560 0.453859 0.058 Uiso 1 1 calc R . . . .
C7 C 0.23248(9) 0.5703(2) 0.72286(17) 0.0488(4) Uani 1 1 d . . . . .
H7A H 0.256724 0.685387 0.723253 0.059 Uiso 1 1 calc R . . . .
H7B H 0.268805 0.491586 0.794221 0.059 Uiso 1 1 calc R . . . .
C8 C 0.16015(9) 0.5862(2) 0.78879(18) 0.0509(4) Uani 1 1 d . . . . .
H8 H 0.174285 0.625519 0.906204 0.061 Uiso 1 1 calc R . . . .
C12 C 0.42859(8) 0.49525(19) 0.14443(17) 0.0484(4) Uani 1 1 d . . . . .
C9 C 0.09352(9) 0.7008(2) 0.6944(2) 0.0634(4) Uani 1 1 d . . . . .
H9A H 0.091451 0.817124 0.743388 0.076 Uiso 1 1 calc R . . . .
H9B H 0.090851 0.709091 0.574507 0.076 Uiso 1 1 calc R . . . .
C10 C 0.03639(10) 0.5692(2) 0.7402(2) 0.0639(5) Uani 1 1 d . . . . .
H10A H -0.005985 0.538466 0.647066 0.077 Uiso 1 1 calc R . . . .
H10B H 0.017538 0.602181 0.838893 0.077 Uiso 1 1 calc R . . . .
C11 C 0.10201(10) 0.4322(2) 0.7752(2) 0.0616(5) Uani 1 1 d . . . . .
H11A H 0.102127 0.352780 0.681754 0.074 Uiso 1 1 calc R . . . .
H11B H 0.105741 0.367096 0.879197 0.074 Uiso 1 1 calc R . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C7 117.80(11) . . ?
C12 O2 H2 109.5 . . ?
O1 C1 C2 115.58(12) . . ?
O1 C1 C6 124.52(12) . . ?
C2 C1 C6 119.90(13) . . ?
C1 C2 H2A 120.0 . . ?
C3 C2 C1 120.05(13) . . ?
C3 C2 H2A 120.0 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.55(13) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C12 120.79(13) . . ?
C5 C4 C3 118.90(13) . . ?
C5 C4 C12 120.30(13) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 C1 119.36(13) . . ?
C5 C6 H6 120.3 . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.20(14) . . ?
C6 C5 H5 119.4 . . ?
O1 C7 H7A 109.9 . . ?
O1 C7 H7B 109.9 . . ?
O1 C7 C8 108.95(12) . . ?
H7A C7 H7B 108.3 . . ?
C8 C7 H7A 109.9 . . ?
C8 C7 H7B 109.9 . . ?
C7 C8 H8 108.7 . . ?
C7 C8 C9 119.43(12) . . ?
C7 C8 C11 121.60(12) . . ?
C9 C8 H8 108.7 . . ?
C9 C8 C11 87.86(12) . . ?
C11 C8 H8 108.7 . . ?
O2 C12 C4 118.10(13) . . ?
O3 C12 O2 123.17(13) . . ?
O3 C12 C4 118.71(12) . . ?
C8 C9 H9A 113.8 . . ?
C8 C9 H9B 113.8 . . ?
H9A C9 H9B 111.0 . . ?
C10 C9 C8 89.31(13) . . ?
C10 C9 H9A 113.8 . . ?
C10 C9 H9B 113.8 . . ?
C9 C10 H10A 114.0 . . ?
C9 C10 H10B 114.0 . . ?
C9 C10 C11 88.20(12) . . ?
H10A C10 H10B 111.2 . . ?
C11 C10 H10A 114.0 . . ?
C11 C10 H10B 114.0 . . ?
C8 C11 H11A 113.9 . . ?
C8 C11 H11B 113.9 . . ?
C10 C11 C8 88.30(13) . . ?
C10 C11 H11A 113.9 . . ?
C10 C11 H11B 113.9 . . ?
H11A C11 H11B 111.1 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.3577(16) . ?
O1 C7 1.4368(16) . ?
O2 H2 0.8200 . ?
O2 C12 1.2681(17) . ?
O3 C12 1.2643(19) . ?
C1 C2 1.3925(19) . ?
C1 C6 1.394(2) . ?
C2 H2A 0.9300 . ?
C2 C3 1.380(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.393(2) . ?
C4 C5 1.3893(19) . ?
C4 C12 1.4747(19) . ?
C6 H6 0.9300 . ?
C6 C5 1.382(2) . ?
C5 H5 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.502(2) . ?
C8 H8 0.9800 . ?
C8 C9 1.528(2) . ?
C8 C11 1.543(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.524(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.537(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
