A one-pot and two-stage Baeyer–Villiger reaction using 2,2′-diperoxyphenic acid under biomolecule-compatible conditions
Gan, Shaoyan; Yin, Jingru; Yu, Zhiyou; Song, Lijuan; Shi, Lei; Green Chemistry 24 (2022) 2232–2239; doi:10.1039/D1GC04478H

data_7244481
_publ_section_title
;
 A one-pot and two-stage Baeyer--Villiger reaction using
 2,2&#x2032;-diperoxyphenic acid under biomolecule-compatible conditions
;
_journal_issue                   5
_journal_name_full               'Green Chemistry'
_journal_page_first              2232
_journal_page_last               2239
_journal_paper_doi               10.1039/D1GC04478H
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C14 H10 O6'
_chemical_formula_sum            'C14 H10 O6'
_chemical_formula_weight         274.22
_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             2021-03-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-06-10 deposited with the CCDC.	2022-02-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.600(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5207(4)
_cell_length_b                   11.7590(3)
_cell_length_c                   7.7352(2)
_cell_measurement_reflns_used    3247
_cell_measurement_temperature    229.99(10)
_cell_measurement_theta_max      71.4030
_cell_measurement_theta_min      3.2610
_cell_volume                     1219.02(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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_environment      N~2~
_diffrn_ambient_temperature      229.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.967
_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     56.00  81.00   0.50    0.05    --    0.00  32.00-109.00   50
  2  \w    100.00 126.00   0.50    0.05    --   55.87  32.00-109.00   52
  3  \w    106.00 131.00   0.50    0.05    --  111.74  32.00-109.00   50
  4  \w     81.00 129.00   0.50    0.05    --   55.87 125.00-180.00   96
  5  \w     47.00 146.00   0.50    0.05    --  111.74 178.00 -90.00  198
  6  \w     86.00 137.00   0.50    0.05    --   55.87 125.00  90.00  102
  7  \w     79.00 118.00   0.50    0.05    --   55.87 125.00 120.00   78
  8  \w     58.00 145.00   0.50    0.05    --  111.74 178.00  90.00  174
  9  \w     35.00  60.00   0.50    0.05    --  111.74  32.00-109.00   50
 10  \w    128.00 153.00   0.50    0.05    --  111.74 -50.00-180.00   50
 11  \w     66.00 111.00   0.50    0.05    --   55.87-125.00 -60.00   90
 12  \w     34.00  60.00   0.50    0.05    --   55.87-125.00 -60.00   52
 13  \w     23.00  69.00   0.50    0.05    --  111.74-111.00 -30.00   92
 14  \w     18.00 101.00   0.50    0.05    --  111.74 -91.00-120.00  166
 15  \w     28.00 117.00   0.50    0.05    --  111.74 -50.00-180.00  178
 16  \w     22.00  47.00   0.50    0.05    --    0.00  32.00-109.00   50
 17  \w    -33.00 124.00   0.50    0.05    --   55.87 -32.00  90.00  314
 18  \w     82.00 108.00   0.50    0.05    --  111.74 -32.00  90.00   52
 19  \w     61.00 106.00   0.50    0.05    --  111.74-111.00 120.00   90
 20  \w     22.00  47.00   0.50    0.05    --  111.74-111.00 120.00   50
 21  \w     22.00  47.00   0.50    0.05    --  111.74 -32.00  90.00   50
 22  \w    -76.00 -28.00   0.50    0.05    --    0.00  32.00-109.00   96
 23  \w   -127.00 -70.00   0.50    0.05    -- -102.00 -32.00  90.00  114
 24  \w    -62.00 -19.00   0.50    0.05    -- -102.00  37.00 120.00   86
 25  \w   -159.00-107.00   0.50    0.05    -- -102.00  37.00 120.00  104
 26  \w   -173.00-131.00   0.50    0.05    -- -102.00 -32.00  90.00   84
 27  \w    -83.00 -46.00   0.50    0.05    --    0.00 178.00-180.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0873881000
_diffrn_orient_matrix_UB_12      0.0529274000
_diffrn_orient_matrix_UB_13      0.1213835000
_diffrn_orient_matrix_UB_21      0.0666280000
_diffrn_orient_matrix_UB_22      -0.0091284000
_diffrn_orient_matrix_UB_23      -0.1463505000
_diffrn_orient_matrix_UB_31      -0.0336637000
_diffrn_orient_matrix_UB_32      0.1195138000
_diffrn_orient_matrix_UB_33      -0.0649422000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6127
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.779
_diffrn_reflns_theta_min         3.298
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.014
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2317
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0522
_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^)+(0.0993P)^2^+0.3424P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1475
_refine_ls_wR_factor_ref         0.1525
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2081
_reflns_number_total             2317
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1gc04478h2.cif
_cod_data_source_block           gsy2021329-s
_cod_depositor_comments          'Adding full bibliography for 7244481.cif.'
_cod_database_code               7244481
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H O'
_shelx_estimated_absorpt_t_max   0.823
_shelx_estimated_absorpt_t_min   0.751
_diffrn_oxdiff_digest_frames
;
0154c746d4d3f3abecfc313b8bad72b4df0005043a2
;
_diffrn_oxdiff_digest_hkl
;
017d8e9ce8ba08efe582c8342380cb4e4b32f2
;
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6A), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13)
2.b Idealised tetrahedral OH refined as rotating group:
 O3(H3), O6(H6)
;
_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 2.058
_oxdiff_exptl_absorpt_empirical_full_min 0.321