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_1567167
_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_absolute_configuration ad
_chemical_formula_moiety         'C16 H14 O2'
_chemical_formula_sum            'C16 H14 O2'
_chemical_formula_weight         238.288
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_Int_Tables_number      19
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-04-04
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2022.03.08 svn.r54f81f84 for OlexSys, GUI svn.r6487)
;
_audit_update_record
;
2022-04-04 deposited with the CCDC.	2022-06-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.9107(1)
_cell_length_b                   13.8035(3)
_cell_length_c                   15.3174(3)
_cell_measurement_reflns_used    5345
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      77.1430
_cell_measurement_theta_min      4.3250
_cell_volume                     1249.72(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-alpha (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9970
_diffrn_measured_fraction_theta_max 0.9647
_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    -24.00  27.00   0.50    0.05    --   47.57 -29.00  24.00  102
  2  \w    -27.00  21.00   0.50    0.05    --   47.57 -19.00 -90.00   96
  3  \w    -18.00  13.00   0.50    0.05    --   47.57 -19.00-120.00   62
  4  \w     61.00  94.00   0.50    0.05    --   47.57  29.00-174.00   66
  5  \w    118.00 172.00   0.50    0.05    --  107.75  57.00 -90.00  108
  6  \w   -112.00 -87.00   0.50    0.05    -- -100.00 -29.00  24.00   50
  7  \w    -92.00 -62.00   0.50    0.05    --  -47.57-155.00 157.00   60
  8  \w   -141.00-115.00   0.50    0.05    -- -100.00 -29.00  24.00   52
  9  \w   -173.00 -88.00   0.50    0.05    -- -100.00 -96.00-150.00  170
 10  \w    -69.00 -42.00   0.50    0.05    -- -100.00  57.00-180.00   54
 11  \w   -102.00 -62.00   0.50    0.05    -- -100.00 125.00 -90.00   80
 12  \w    -52.00 -27.00   0.50    0.05    -- -100.00 125.00 -90.00   50
 13  \w   -109.00 -28.00   0.50    0.05    -- -100.00 119.00  39.00  162
 14  \w     41.00  89.00   0.50    0.05    --  107.75 -99.00  90.00   96
 15  \w     41.00  97.00   0.50    0.05    --  107.75-125.00 -90.00  112
 16  \w     37.00  62.00   0.50    0.05    --  107.75 -57.00 -90.00   50
 17  \w     76.00 101.00   0.50    0.05    --  107.75 -77.00-150.00   50
 18  \w     35.00  60.00   0.50    0.05    --  107.75 -57.00-180.00   50
 19  \w     68.00 102.00   0.50    0.05    --  107.75 -77.00  60.00   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0225478000
_diffrn_orient_matrix_UB_12      0.1106232000
_diffrn_orient_matrix_UB_13      -0.0094823000
_diffrn_orient_matrix_UB_21      0.2429600000
_diffrn_orient_matrix_UB_22      -0.0050348000
_diffrn_orient_matrix_UB_23      0.0362096000
_diffrn_orient_matrix_UB_31      0.0921175000
_diffrn_orient_matrix_UB_32      -0.0132365000
_diffrn_orient_matrix_UB_33      -0.0933578000
_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  0.0289
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.9970
_diffrn_reflns_Laue_measured_fraction_max 0.9647
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6468
_diffrn_reflns_point_group_measured_fraction_full 0.9956
_diffrn_reflns_point_group_measured_fraction_max 0.9353
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         77.46
_diffrn_reflns_theta_min         4.31
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.658
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66880
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.103a (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    1.266
_exptl_crystal_description       plate
_exptl_crystal_F_000             505.648
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.6592
_refine_diff_density_min         -0.2498
_refine_diff_density_rms         0.0521
_refine_ls_abs_structure_details
'Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.'
_refine_ls_abs_structure_Flack   -0.24(10)
_refine_ls_d_res_high            0.7898
_refine_ls_d_res_low             10.2541
_refine_ls_goodness_of_fit_ref   1.0551
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    27
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2485
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0551
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0467
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0669P)^2^+0.5666P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1230
_refine_ls_wR_factor_ref         0.1242
_reflns_Friedel_coverage         0.893
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              17
_reflns_limit_k_min              -16
_reflns_limit_l_max              18
_reflns_limit_l_min              -18
_reflns_number_gt                2400
_reflns_number_total             2485
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d2sc02079c2.cif
_cod_data_source_block           zhangchangsheng_0621_auto
_cod_depositor_comments
'Adding full bibliography for 1567165--1567169.cif.'
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               1567167
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9a,H9b)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16)
;
_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 1.529
_oxdiff_exptl_absorpt_empirical_full_min 0.484