Cu(ii)/SPDO complex catalyzed asymmetric Baeyer-Villiger oxidation of 2-arylcyclobutanones and its application for the total synthesis of eupomatilones 5 and 6.
Zhang, Chang-Sheng; Shao, Ya-Ping; Zhang, Fu-Min; Han, Xue; Zhang, Xiao-Ming; Zhang, Kun; Tu, Yong-Qiang; Chemical science 13 (2022) 8429–8435; doi:10.1039/d2sc02079c

data_1567169
_publ_section_title
;
 Cu(ii)/SPDO complex catalyzed asymmetric Baeyer-Villiger oxidation of
 2-arylcyclobutanones and its application for the total synthesis of
 eupomatilones 5 and 6.
;
_journal_issue                   28
_journal_name_full               'Chemical science'
_journal_page_first              8429
_journal_page_last               8435
_journal_paper_doi               10.1039/d2sc02079c
_journal_volume                  13
_journal_year                    2022
_chemical_formula_moiety         'C14 H17 Br O5'
_chemical_formula_sum            'C14 H17 Br O5'
_chemical_formula_weight         345.18
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-09-27
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-04-04 deposited with the CCDC.	2022-06-22 downloaded from the CCDC.
;
_cell_angle_alpha                94.2410(10)
_cell_angle_beta                 94.434(2)
_cell_angle_gamma                111.794(2)
_cell_formula_units_Z            2
_cell_length_a                   7.8803(2)
_cell_length_b                   9.7157(2)
_cell_length_c                   10.6212(2)
_cell_measurement_reflns_used    6963
_cell_measurement_temperature    303.15(10)
_cell_measurement_theta_max      76.2170
_cell_measurement_theta_min      4.1930
_cell_volume                     748.16(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      303.15(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.955
_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     42.00 119.00   0.50    0.05    --   46.32  54.00 135.00  154
  2  \w     91.00 170.00   0.50    0.05    --  104.25  54.00 135.00  158
  3  \w    142.00 173.00   0.50    0.05    --  104.25  45.00  60.00   62
  4  \w    102.00 134.00   0.50    0.05    --  104.25  45.00  60.00   64
  5  \w    132.00 173.00   0.50    0.05    --  104.25  15.00-120.00   82
  6  \w     94.00 120.00   0.50    0.05    --  104.25  15.00-120.00   52
  7  \w     95.00 121.00   0.50    0.05    --  104.25  30.00-180.00   52
  8  \w    126.00 178.00   0.50    0.05    --  104.25  30.00-180.00  104
  9  \w     92.00 176.00   0.50    0.05    --  104.25  61.00-150.00  168
 10  \w    -14.00  28.00   0.50    0.05    --   46.32 -19.00-150.00   84
 11  \w    -27.00  29.00   0.50    0.05    --   46.32 -19.00   0.00  112
 12  \w    -25.00   5.00   0.50    0.05    --   46.32 -54.00  -8.00   60
 13  \w     -7.00  44.00   0.50    0.05    --   46.32 -37.00 -90.00  102
 14  \w     34.00  64.00   0.50    0.05    --  104.25 -54.00  -8.00   60
 15  \w     51.00  88.00   0.50    0.05    --  104.25 -77.00-120.00   74
 16  \w     34.00  72.00   0.50    0.05    --  104.25 -61.00 -30.00   76
 17  \w     43.00  73.00   0.50    0.05    --  104.25 -61.00 150.00   60
 18  \w     61.00  95.00   0.50    0.05    --  104.25 -94.00 150.00   68
 19  \w     74.00 112.00   0.50    0.05    --  104.25-125.00  90.00   76
 20  \w     41.00 112.00   0.50    0.05    --  104.25-125.00  60.00  142
 21  \w     36.00 104.00   0.50    0.05    --  104.25 -94.00  90.00  136
 22  \w     32.00  93.00   0.50    0.05    --  104.25-125.00   0.00  122
 23  \w     62.00  87.00   0.50    0.05    --  104.25-125.00 -60.00   50
 24  \w     82.00 112.00   0.50    0.05    --  104.25-125.00 -90.00   60
 25  \w     37.00  92.00   0.50    0.05    --  104.25 -94.00 -60.00  110
 26  \w     41.00  99.00   0.50    0.05    --  104.25 -94.00-180.00  116
 27  \w    -69.00 -33.00   0.50    0.05    -- -102.00  61.00 -60.00   72
 28  \w    -67.00 -31.00   0.50    0.05    -- -102.00  61.00 -90.00   72
 29  \w    -67.00 -35.00   0.50    0.05    -- -102.00  61.00  90.00   64
 30  \w    -59.00 -29.00   0.50    0.05    -- -102.00  54.00 135.00   60
 31  \w    -56.00  -1.00   0.50    0.05    --  -46.32  54.00 135.00  110
 32  \w   -120.00 -94.00   0.50    0.05    -- -102.00 136.00  78.38   52
 33  \w    -68.00 -36.00   0.50    0.05    --  -46.32 -54.00  -8.00   64
 34  \w   -114.00 -89.00   0.50    0.05    --  -46.32 -54.00  -8.00   50
 35  \w   -167.00-141.00   0.50    0.05    -- -102.00 -54.00  -8.00   52
 36  \w   -140.00-106.00   0.50    0.05    -- -102.00 -54.00  -8.00   68
 37  \w   -116.00 -81.00   0.50    0.05    --  -46.32-125.00 -60.00   70
 38  \w   -159.00 -75.00   0.50    0.05    -- -102.00-125.00   0.00  168
;
_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      0.1447049000
_diffrn_orient_matrix_UB_12      0.1402530000
_diffrn_orient_matrix_UB_13      -0.0421787000
_diffrn_orient_matrix_UB_21      -0.1519327000
_diffrn_orient_matrix_UB_22      0.0238946000
_diffrn_orient_matrix_UB_23      -0.0850385000
_diffrn_orient_matrix_UB_31      -0.0296753000
_diffrn_orient_matrix_UB_32      0.0963515000
_diffrn_orient_matrix_UB_33      0.1114347000
_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  0.0248
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8578
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.451
_diffrn_reflns_theta_min         4.201
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.900
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69485
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.105a (Rigaku Oxford Diffraction, 2021)
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    1.532
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2995
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0306
_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^)+(0.0440P)^2^+0.1921P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0819
_refine_ls_wR_factor_ref         0.0832
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2761
_reflns_number_total             2995
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc02079c2.cif
_cod_data_source_block           zhangchangsheng_0918-1_auto
_cod_depositor_comments
'Adding full bibliography for 1567165--1567169.cif.'
_cod_database_code               1567169
_shelx_shelxl_version_number     2018/1
_reflns_odcompleteness_completeness 99.48
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C10(H10), C11(H11)
1.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
1.c Aromatic/amide H refined with riding coordinates:
 C3(H3)
1.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C14(H14A,H14B,H14C)
;
_shelx_res_checksum              28056
_shelx_hkl_checksum              30610
_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 3.745
_oxdiff_exptl_absorpt_empirical_full_min 0.575