First total synthesis of asperilactone B. Revision of absolute stereochemistry of asperilactones B and C.
Djokić, Sanja; Benedeković, Goran; Kesić, Jelena; Rodić, Marko V; Popsavin, Mirjana; Popsavin, Velimir; Francuz, Jovana; Organic & biomolecular chemistry 22 (2024) 4864–4867; doi:10.1039/d4ob00583j

data_7159947
_publ_section_title
;
 First total synthesis of asperilactone B. Revision of absolute
 stereochemistry of asperilactones B and C.
;
_journal_issue                   24
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4864
_journal_page_last               4867
_journal_paper_doi               10.1039/d4ob00583j
_journal_volume                  22
_journal_year                    2024
_chemical_absolute_configuration rm
_chemical_enantioexcess_bulk     1
_chemical_enantioexcess_bulk_technique OA
_chemical_formula_moiety         'C8 H12 O5'
_chemical_formula_sum            'C8 H12 O5'
_chemical_formula_weight         188.18
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2024-02-19 deposited with the CCDC.	2024-05-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.269(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.5474(5)
_cell_length_b                   5.4514(3)
_cell_length_c                   9.7185(6)
_cell_measurement_reflns_used    4551
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.3330
_cell_measurement_theta_min      2.7350
_cell_volume                     427.47(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2020)'
_computing_publication_material  'ShelXle (H\"ubschle et al., 2011)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.3280
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.916
_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    -83.00   1.00   1.00   20.00    --  -15.69 -57.00-180.00   84
  2  \w    -39.00  11.00   1.00   20.00    --  -15.69 -77.00 120.00   50
  3  \w    -39.00  11.00   1.00   20.00    --  -15.69 -77.00  30.00   50
  4  \w    -42.00  18.00   1.00   20.00    --  -15.69  77.00 -60.00   60
  5  \w    -53.00  86.00   1.00   20.00    --   16.71   0.00-120.00  139
  6  \w    -20.00  55.00   1.00   20.00    --   16.71 -99.00  60.00   75
  7  \w    -39.00  11.00   1.00   20.00    --  -15.69 -77.00-120.00   50
  8  \w    -39.00  11.00   1.00   20.00    --  -15.69 -77.00 -30.00   50
  9  \w    -42.00  18.00   1.00   20.00    --  -15.69  77.00 120.00   60
 10  \w    -39.00  43.00   1.00   20.00    --   16.71 -77.00-150.00   82
 11  \w    -55.00  46.00   1.00   20.00    --   16.71 -19.00 120.00  101
 12  \w    -39.00  11.00   1.00   20.00    --  -15.69 -77.00   0.00   50
 13  \w    -20.00  55.00   1.00   20.00    --   16.71 -99.00 -90.00   75
 14  \w    -39.00  43.00   1.00   20.00    --   16.71 -77.00-120.00   82
 15  \w     -2.00  86.00   1.00   20.00    --   16.71  37.00 -30.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Gemini S (Oxford Diffraction)'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0673457000
_diffrn_orient_matrix_UB_12      -0.0099346000
_diffrn_orient_matrix_UB_13      -0.0269973000
_diffrn_orient_matrix_UB_21      0.0561923000
_diffrn_orient_matrix_UB_22      0.0255020000
_diffrn_orient_matrix_UB_23      0.0705954000
_diffrn_orient_matrix_UB_31      0.0059368000
_diffrn_orient_matrix_UB_32      -0.1272228000
_diffrn_orient_matrix_UB_33      0.0162685000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.916
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10436
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.883
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.393
_diffrn_reflns_theta_min         2.220
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91585
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 

Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_description       plate
_exptl_crystal_F_000             200
_exptl_crystal_size_max          0.804
_exptl_crystal_size_mid          0.139
_exptl_crystal_size_min          0.068
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
; 
 Flack x determined using 703 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 

_refine_ls_abs_structure_Flack    -2.4(5) 

 The absolute structure parameter is meaningless because the compound is a 
 weak anomalous scatterer.
;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     123
_refine_ls_number_reflns         2091
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0363
_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^)+(0.0380P)^2^+0.0518P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0841
_reflns_Friedel_coverage         0.754
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.843
_reflns_number_gt                1835
_reflns_number_total             2091
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00583j3.cif
_cod_data_source_block           10
_cod_depositor_comments
'Adding full bibliography for 7159944--7159948.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7159947
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.908
_shelx_estimated_absorpt_t_max   0.992
_shelx_res_checksum              45532