Total synthesis of (±)-halichonine B.
Yoshimura, Fumihiko; Uchida, Masaya; Aratame, Kaori; Ouchi, Hitoshi; Inai, Makoto; Kondo, Mitsuru; Takita, Ryo; Kan, Toshiyuki; Organic & biomolecular chemistry 23 (2025) 3076–3080; doi:10.1039/d5ob00145e

data_7160395
_publ_section_title
;
 Total synthesis of (&#xb1;)-halichonine B.
;
_journal_issue                   13
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3076
_journal_page_last               3080
_journal_paper_doi               10.1039/d5ob00145e
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C16 H26 O2'
_chemical_formula_sum            'C16 H26 O2'
_chemical_formula_weight         250.37
_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     dual
_audit_creation_date             2024-03-04
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-03-28 deposited with the CCDC.	2025-02-25 downloaded from the CCDC.
;
_cell_angle_alpha                110.304(3)
_cell_angle_beta                 90.564(2)
_cell_angle_gamma                98.950(2)
_cell_formula_units_Z            2
_cell_length_a                   6.14260(10)
_cell_length_b                   9.4202(3)
_cell_length_c                   13.5004(4)
_cell_measurement_reflns_used    5437
_cell_measurement_temperature    173.01(10)
_cell_measurement_theta_max      74.5700
_cell_measurement_theta_min      3.4800
_cell_volume                     722.01(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.102a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.102a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.102a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.960
_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     69.00  94.00   0.50    0.20    --   42.25 134.00  24.00   50
  2  \w     87.00 113.00   0.50    0.30    --  109.37 134.00  24.00   52
  3  \w     98.00 123.00   0.50    0.30    --  109.37 137.00-157.00   50
  4  \w    122.00 162.00   0.50    0.30    --  109.37  61.00-150.00   80
  5  \w     91.00 116.00   0.50    0.30    --  109.37  61.00-150.00   50
  6  \w     89.00 114.00   0.50    0.20    --   42.25 137.00-157.00   50
  7  \w   -173.00 -28.00   0.50    0.30    -- -106.00   0.00 120.00  290
  8  \w    -72.00 -47.00   0.50    0.30    -- -106.00  61.00 150.00   50
  9  \w    -65.00 -34.00   0.50    0.30    -- -106.00  61.00  30.00   62
 10  \w   -105.00 -70.00   0.50    0.30    -- -106.00  77.00-150.00   70
 11  \w    -60.00 -34.00   0.50    0.30    -- -106.00  77.00-150.00   52
 12  \w    -26.00  36.00   0.50    0.20    --  -42.25  19.00-150.00  124
 13  \w    -34.00  25.00   0.50    0.20    --   42.25 -19.00 -60.00  118
 14  \w     -4.00  23.00   0.50    0.20    --   42.25 -19.00 -30.00   54
 15  \w    -37.00  -5.00   0.50    0.20    --   42.25 -19.00 -90.00   64
 16  \w    -38.00  24.00   0.50    0.20    --   42.25 -19.00-150.00  124
 17  \w     35.00  61.00   0.50    0.30    --  109.37 -95.00 -30.00   52
 18  \w     54.00  97.00   0.50    0.30    --  109.37-134.00 -42.00   86
 19  \w     58.00 100.00   0.50    0.20    --   42.25-134.00 -42.00   84
 20  \w     84.00 110.00   0.50    0.30    --  109.37-125.00  30.00   52
 21  \w     80.00 118.00   0.50    0.30    --  109.37-137.00 139.00   76
 22  \w     71.00 105.00   0.50    0.30    --  109.37 -95.00 120.00   68
 23  \w     35.00  63.00   0.50    0.30    --  109.37 -95.00 120.00   56
 24  \w     55.00  92.00   0.50    0.20    --   42.25-137.00 139.00   74
 25  \w     70.00 106.00   0.50    0.30    --  109.37 -95.00 -30.00   72
 26  \w     77.00 103.00   0.50    0.30    --  109.37 -77.00 -30.00   52
 27  \w     42.00  68.00   0.50    0.30    --  109.37 -61.00 -60.00   52
 28  \w     39.00  68.00   0.50    0.30    --  109.37 -61.00 -90.00   58
 29  \w     35.00  72.00   0.50    0.30    --  109.37 -77.00 -30.00   74
 30  \w     36.00  69.00   0.50    0.30    --  109.37 -61.00 120.00   66
 31  \w     41.00  69.00   0.50    0.30    --  109.37 -61.00 150.00   56
 32  \w     37.00  65.00   0.50    0.30    --  109.37 -61.00  90.00   56
 33  \w    -71.00 -46.00   0.50    0.20    --  -42.25 137.00-157.00   50
 34  \w    -97.00 -31.00   0.50    0.30    -- -106.00 137.00-157.00  132
 35  \w   -108.00 -80.00   0.50    0.30    -- -106.00 111.00-104.52   56
 36  \w    -71.00 -32.00   0.50    0.30    -- -106.00 111.00-104.52   78
 37  \w    -80.00 -55.00   0.50    0.30    -- -106.00 134.00  24.00   50
 38  \w   -112.00 -73.00   0.50    0.30    -- -106.00 125.00 150.00   78
 39  \w    -77.00 -45.00   0.50    0.20    --  -42.25 134.00  24.00   64
 40  \w   -177.00-134.00   0.50    0.30    -- -106.00 -30.00   0.00   86
 41  \w   -116.00 -91.00   0.50    0.20    --  -42.25-137.00 139.00   50
 42  \w   -115.00 -73.00   0.50    0.20    --  -42.25-134.00 -42.00   84
 43  \w   -113.00 -84.00   0.50    0.30    -- -106.00 -30.00   0.00   58
 44  \w   -122.00 -83.00   0.50    0.30    -- -106.00 -95.00  90.00   78
 45  \w   -176.00-128.00   0.50    0.30    -- -106.00 -95.00  90.00   96
 46  \w   -172.00-145.00   0.50    0.30    -- -106.00-134.00 -42.00   54
 47  \w   -123.00 -95.00   0.50    0.30    -- -106.00-134.00 -42.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0143541000
_diffrn_orient_matrix_UB_12      0.0863234000
_diffrn_orient_matrix_UB_13      0.1205290000
_diffrn_orient_matrix_UB_21      0.0032419000
_diffrn_orient_matrix_UB_22      0.1526907000
_diffrn_orient_matrix_UB_23      -0.0185547000
_diffrn_orient_matrix_UB_31      -0.2540679000
_diffrn_orient_matrix_UB_32      -0.0232202000
_diffrn_orient_matrix_UB_33      -0.0018445000
_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  0.0242
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6991
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.910
_diffrn_reflns_theta_min         3.499
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.572
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76398
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.102a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_description       block
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2850
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0505
_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^)+(0.1022P)^2^+0.0923P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1466
_refine_ls_wR_factor_ref         0.1496
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2589
_reflns_number_total             2850
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00145e2.cif
_cod_data_source_block           20240304-cooh-utm-a_auto
_cod_depositor_comments          'Adding full bibliography for 7160395.cif.'
_cod_database_code               7160395
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C16H26O2
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C2(H2A,H2B), C6(H6A,H6B), C8(H8A,H8B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14)
2.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C16(H16A,H16B,H16C), C11(H11A,H11B,H11C), C10(H10A,H10B,H10C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              29460
_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 2.060
_oxdiff_exptl_absorpt_empirical_full_min 0.468