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_7158651
_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         'C17 H22 O5'
_chemical_formula_sum            'C17 H22 O5'
_chemical_formula_weight         306.34
_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     SHELXT
_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                75.4950(10)
_cell_angle_beta                 84.8940(10)
_cell_angle_gamma                88.4970(10)
_cell_formula_units_Z            4
_cell_length_a                   8.78440(10)
_cell_length_b                   10.21930(10)
_cell_length_c                   18.8935(2)
_cell_measurement_reflns_used    8635
_cell_measurement_temperature    99.96(2)
_cell_measurement_theta_max      28.7390
_cell_measurement_theta_min      2.2220
_cell_volume                     1635.49(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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_temperature      99.96(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_measured_fraction_theta_full 0.912
_diffrn_measured_fraction_theta_max 0.695
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \f   -180.00 180.00   0.10    0.03   0.00   0.00   0.00    --  3600
;
_diffrn_measurement_device_type  'Dectris Eiger2 9M'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0249881000
_diffrn_orient_matrix_UB_12      0.0166497000
_diffrn_orient_matrix_UB_13      -0.0379111000
_diffrn_orient_matrix_UB_21      -0.0658410000
_diffrn_orient_matrix_UB_22      -0.0313201000
_diffrn_orient_matrix_UB_23      -0.0074076000
_diffrn_orient_matrix_UB_31      -0.0401560000
_diffrn_orient_matrix_UB_32      0.0623042000
_diffrn_orient_matrix_UB_33      -0.0047534000
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_Laue_measured_fraction_full 0.912
_diffrn_reflns_Laue_measured_fraction_max 0.695
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            21093
_diffrn_reflns_point_group_measured_fraction_full 0.912
_diffrn_reflns_point_group_measured_fraction_max 0.695
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.175
_diffrn_reflns_theta_min         1.117
_diffrn_source                   'MX1 Beamline Australian Synchrotron'
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.94554
_exptl_absorpt_correction_T_min  0.94554
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Spherical absorption correction
using equivalent radius and absorption coefficient.
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    1.244
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_crystal_size_rad          0.395
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     405
_refine_ls_number_reflns         6141
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.1028
_refine_ls_R_factor_gt           0.0673
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1223P)^2^+0.2529P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1844
_refine_ls_wR_factor_ref         0.2120
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3942
_reflns_number_total             6141
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00651k2.cif
_cod_data_source_block           tfmr1asyn
_cod_depositor_comments
'Adding full bibliography for 7158650--7158653.cif.'
_cod_database_code               7158651
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C17H22O5
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.994
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C2(H2), C5(H5), C2A(H2A), C5A(H5A)
1.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C9(H9A,H9B), C4A(H4AA,H4AB), C9A(H9AA,H9AB)
1.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C14(H14), C15(H15), C11A(H11A), C12A(H12A), C14A(H14A),
 C15A(H15A)
1.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C3(H3A,H3B,H3C), C7(H7A,H7B,H7C), C17(H17A,H17B,H17C),
 C1A(H1AA,H1AB,H1AC), C3A(H3AA,H3AB,H3AC), C7A(H7AA,H7AB,H7AC), C17A(H17D,H17E,
 H17F)
;
_shelx_res_checksum              96552
_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 1.401
_oxdiff_exptl_absorpt_empirical_full_min 0.811