Synthesis of acyloin natural products by Mukaiyama hydration.
Ricca, Michael; Zhang, Wei; Li, Jiaqi; Fellowes, Thomas; White, Jonathan M.; Donnelly, Paul S.; Rizzacasa, Mark A.; Organic & biomolecular chemistry 20 (2022) 4038–4047; doi:10.1039/d2ob00651k

data_7158652
_publ_section_title
;
 Synthesis of acyloin natural products by Mukaiyama hydration.
;
_journal_issue                   19
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4038
_journal_page_last               4047
_journal_paper_doi               10.1039/d2ob00651k
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C21 H26 N2 O4, C H4 O'
_chemical_formula_sum            'C22 H30 N2 O5'
_chemical_formula_weight         402.48
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-08-29
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-08-31 deposited with the CCDC.	2022-04-25 downloaded from the CCDC.
;
_cell_angle_alpha                67.3400(10)
_cell_angle_beta                 80.5230(10)
_cell_angle_gamma                88.5940(10)
_cell_formula_units_Z            2
_cell_length_a                   8.36320(10)
_cell_length_b                   10.77980(10)
_cell_length_c                   12.6342(2)
_cell_measurement_reflns_used    33002
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      44.4210
_cell_measurement_theta_min      2.4600
_cell_volume                     1035.80(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_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     36.00 114.00   0.50    3.21    --   42.08  37.00  60.00  156
  2  \w     85.00 111.00   0.50    3.21    --   42.08  57.00 120.00   52
  3  \w     83.00 114.00   0.50    3.21    --   42.08  57.00 150.00   62
  4  \w     65.00  90.00   0.50    3.21    --   42.08 136.00  46.00   50
  5  \w     85.00 113.00   0.50    3.21    --   42.08 178.00   0.00   56
  6  \w     58.00  83.00   0.50    3.21    --   42.08 178.00   0.00   50
  7  \w     63.00 114.00   0.50    3.21    --   42.08 178.00  30.00  102
  8  \w     54.00  96.00   0.50    3.21    --   42.08 178.00  90.00   84
  9  \w     50.00  76.00   0.50    3.21    --   42.08 178.00  60.00   52
 10  \w     50.00  83.00   0.50    3.21    --   42.08 178.00 -90.00   66
 11  \w     89.00 115.00   0.50    3.21    --   42.08 178.00-150.00   52
 12  \w     66.00  91.00   0.50    3.21    --   42.08 133.00-131.00   50
 13  \w     69.00 114.00   0.50    3.21    --   42.08  37.00 -60.00   90
 14  \w     35.00  60.00   0.50    3.21    --   42.08 -75.00-114.49   50
 15  \w     44.00  76.00   0.50    3.21    --   42.08 -99.00-150.00   64
 16  \w     35.00  62.00   0.50    3.21    --   42.08 -77.00-180.00   54
 17  \w     -7.00  45.00   0.50    3.21    --   42.08 -99.00-180.00  104
 18  \w     -8.00  18.00   0.50    3.21    --   42.08 -57.00 -90.00   52
 19  \w     27.00  53.00   0.50    3.21    --   42.08 -99.00 -30.00   52
 20  \w     56.00  90.00   0.50    3.21    --   42.08-136.00 -17.00   68
 21  \w     68.00  93.00   0.50    3.21    --   42.08-133.00  33.14   50
 22  \w     43.00  75.00   0.50    3.21    --   42.08 -99.00  90.00   64
 23  \w     30.00  55.00   0.50    3.21    --   42.08-133.00 160.00   50
 24  \w      5.00  86.00   0.50    3.21    --   42.08-118.00 138.93  162
 25  \w     26.00  52.00   0.50    3.21    --   42.08 -77.00  30.00   52
 26  \w     -5.00  31.00   0.50    3.21    --   42.08 -99.00  90.00   72
 27  \w     -9.00  17.00   0.50    3.21    --   42.08 -57.00  30.00   52
 28  \w     -7.00  73.00   0.50    3.21    --   42.08 -99.00   0.00  160
 29  \w     76.00 109.00   0.50    3.21    --   42.08-178.00 -90.00   66
 30  \w     54.00  79.00   0.50    3.21    --   42.08-165.00-123.86   50
 31  \w     -1.00  25.00   0.50    3.21    --   42.08 -75.00-132.43   52
 32  \w    -13.00  12.00   0.50    3.21    --   42.08 -37.00-120.00   50
 33  \w    -31.00  -6.00   0.50    3.21    --   42.08 -37.00 -90.00   50
 34  \w    -17.00  12.00   0.50    3.21    --   42.08 -37.00 -60.00   58
 35  \w    -23.00   2.00   0.50    3.21    --   42.08 -57.00-120.00   50
 36  \w    -24.00  11.00   0.50    3.21    --   42.08 -77.00-150.00   70
 37  \w    -25.00  20.00   0.50    3.21    --   42.08 -77.00-180.00   90
 38  \w     35.00  61.00   0.50    3.21    --   42.08  37.00 -90.00   52
 39  \w     40.00  65.00   0.50    3.21    --   42.08  19.00   0.00   50
 40  \w     40.00  65.00   0.50    3.21    --   42.08  37.00  90.00   50
 41  \w    -20.00  10.00   0.50    3.21    --   42.08 -37.00  90.00   60
 42  \w    -21.00   4.00   0.50    3.21    --   42.08 -37.00  60.00   50
 43  \w    -56.00 -30.00   0.50    3.21    --  -41.30 -57.00 120.00   52
 44  \w    -83.00 -49.00   0.50    3.21    --  -41.30 113.00  -7.93   68
 45  \w    -94.00 -68.00   0.50    3.21    --  -41.30 136.00  46.00   52
 46  \w    -93.00 -68.00   0.50    3.21    --  -41.30 133.00-131.00   50
 47  \w    -87.00 -62.00   0.50    3.21    --  -41.30 121.00 -75.24   50
 48  \w   -101.00 -76.00   0.50    3.21    --  -41.30 145.00-100.29   50
 49  \w    -91.00 -66.00   0.50    3.21    --  -41.30 129.00 119.36   50
 50  \w    -88.00 -63.00   0.50    3.21    --  -41.30 123.00 167.87   50
 51  \w    -86.00 -61.00   0.50    3.21    --  -41.30 119.00 134.41   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0062072000
_diffrn_orient_matrix_UB_12      -0.0240044000
_diffrn_orient_matrix_UB_13      0.0598607000
_diffrn_orient_matrix_UB_21      -0.0848689000
_diffrn_orient_matrix_UB_22      -0.0147910000
_diffrn_orient_matrix_UB_23      0.0150081000
_diffrn_orient_matrix_UB_31      0.0128713000
_diffrn_orient_matrix_UB_32      -0.0655628000
_diffrn_orient_matrix_UB_33      0.0006715000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            61757
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.318
_diffrn_reflns_theta_min         2.129
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.556
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.349
_exptl_crystal_size_mid          0.196
_exptl_crystal_size_min          0.158
_refine_diff_density_max         0.598
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         10019
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0679P)^2^+0.1561P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1172
_refine_ls_wR_factor_ref         0.1223
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8443
_reflns_number_total             10019
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00651k2.cif
_cod_data_source_block           tf-mr2-mo
_cod_depositor_comments
'Adding full bibliography for 7158650--7158653.cif.'
_cod_database_code               7158652
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_olex2_refinement_description
;
1. Restrained distances
 O5-H5 \\sim O5A-H5
 with sigma of 0.02
 O5-C5 \\sim O5A-C5
 with sigma of 0.02
2. Others
 Sof(H5BE)=Sof(H5BF)=Sof(H5BD)=Sof(O5A)=1-FVAR(1)
 Sof(O5)=Sof(H5AB)=Sof(H5AC)=Sof(H5AA)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C8(H8A,H8B), C20(H20A,H20B), C18(H18A,H18B)
3.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C23(H23), C15(H15), C13(H13), C14(H14), C7(H7), C4(H4), C3(H3)
3.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C19(H19A,H19B,H19C), C5(H5AB,H5AC,H5AA), C5(H5BE,H5BF,
 H5BD)
;
_shelx_res_checksum              87209
_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 1.212
_oxdiff_exptl_absorpt_empirical_full_min 0.891