High-yielding total synthesis of embelin, rapanone, and irisoquin A, D, F.
Ashok, Etikala; Lakshmi, Pandhiti R.; Sanwal, Shyam D.; Ramachary, Dhevalapally B.; Organic & biomolecular chemistry 23 (2025) 2195–2205; doi:10.1039/d4ob01706d

data_7160338
_publ_section_title
;
 High-yielding total synthesis of embelin, rapanone, and irisoquin A, D,
 F.
;
_journal_issue                   9
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2195
_journal_page_last               2205
_journal_paper_doi               10.1039/d4ob01706d
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C20 H32 O4'
_chemical_formula_sum            'C20 H32 O4'
_chemical_formula_weight         336.45
_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             2023-04-26
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_audit_update_record
;
2024-09-26 deposited with the CCDC.	2025-01-16 downloaded from the CCDC.
;
_cell_angle_alpha                86.035(2)
_cell_angle_beta                 83.345(2)
_cell_angle_gamma                80.582(2)
_cell_formula_units_Z            2
_cell_length_a                   5.16170(10)
_cell_length_b                   9.9928(3)
_cell_length_c                   19.9937(5)
_cell_measurement_reflns_used    8780
_cell_measurement_temperature    299.0
_cell_measurement_theta_max      24.9870
_cell_measurement_theta_min      2.0670
_cell_volume                     1009.19(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      299.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.956
_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    -10.00  90.00   0.50   16.00    --   16.22  30.00 -30.00  200
  2  \w     -8.00  86.00   0.50   16.00    --   16.22  45.00  30.00  188
  3  \w    -10.00  90.00   0.50   16.00    --   16.22  30.00  30.00  200
  4  \w    -11.00  86.00   0.50   16.00    --   16.22  61.00  30.00  194
  5  \w      9.00  70.00   0.50   16.00    --   16.22-124.00  98.00  122
  6  \w    -37.00  22.00   0.50   16.00    --  -14.97 -94.00   0.00  118
  7  \w     21.00  86.00   0.50   16.00    --   16.22-147.00 -67.00  130
  8  \w    -41.00  59.00   0.50   16.00    --  -14.97  30.00-120.00  200
  9  \w    -37.00  22.00   0.50   16.00    --  -14.97 -94.00-180.00  118
 10  \w    -54.00  41.00   0.50   16.00    --   16.22 -45.00-150.00  190
 11  \w    -37.00  22.00   0.50   16.00    --  -14.97 -94.00 -90.00  118
 12  \w    -39.00  55.00   0.50   16.00    --  -14.97  45.00   0.00  188
 13  \w    -37.00  22.00   0.50   16.00    --  -14.97 -94.00  60.00  118
 14  \w    -54.00  41.00   0.50   16.00    --   16.22 -45.00  60.00  190
 15  \w    -46.00  58.00   0.50   16.00    --  -14.97  77.00 150.00  208
 16  \w    -54.00  41.00   0.50   16.00    --   16.22 -45.00  30.00  190
 17  \w    -69.00 -10.00   0.50   16.00    --  -14.97 125.00 120.00  118
 18  \w    -69.00  -9.00   0.50   16.00    --  -14.97 124.00 177.00  120
 19  \w    -89.00  10.00   0.50   16.00    --  -14.97 -30.00  60.00  198
 20  \w    -85.00  10.00   0.50   16.00    --  -14.97 -45.00 150.00  190
 21  \w    -82.00 -22.00   0.50   16.00    --  -14.97 147.00 -16.00  120
 22  \w    -69.00 -12.00   0.50   16.00    --  -14.97 125.00 -60.00  114
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0131463000
_diffrn_orient_matrix_UB_12      -0.0534151000
_diffrn_orient_matrix_UB_13      0.0252454000
_diffrn_orient_matrix_UB_21      0.0269381000
_diffrn_orient_matrix_UB_22      -0.0482503000
_diffrn_orient_matrix_UB_23      -0.0252969000
_diffrn_orient_matrix_UB_31      0.1368425000
_diffrn_orient_matrix_UB_32      0.0030469000
_diffrn_orient_matrix_UB_33      -0.0013357000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            24036
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.041
_diffrn_reflns_theta_min         2.054
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40317
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic orangish orange'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.107
_exptl_crystal_description       plate
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         4247
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.1136
_refine_ls_R_factor_gt           0.0657
_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^)+(0.1347P)^2^+0.0229P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2025
_refine_ls_wR_factor_ref         0.2476
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2116
_reflns_number_total             4247
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01706d3.cif
_cod_data_source_block           dbr63
_cod_depositor_comments          'Adding full bibliography for 7160338.cif.'
_cod_database_code               7160338
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.981
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B),
 C9(H9A,H9B), C8(H8A,H8B), C7(H7A,H7B), C10(H10A,H10B), C11(H11A,H11B),
 C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C17(H17)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              24712
_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 1.924
_oxdiff_exptl_absorpt_empirical_full_min 0.588