First synthesis of (±)-halichonadins A-D.
Fujita, Ryohei; Ooka, Kaito; Wasada, Hiroaki; Ichikawa, Yoshiyasu; Hosokawa, Seijiro; Organic & biomolecular chemistry 22 (2024) 1901–1906; doi:10.1039/d4ob00088a

data_7159796
_publ_section_title
;
 First synthesis of (&#xb1;)-halichonadins A-D.
;
_journal_issue                   9
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1901
_journal_page_last               1906
_journal_paper_doi               10.1039/d4ob00088a
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C15 H23 N O'
_chemical_formula_sum            'C15 H23 N O'
_chemical_formula_weight         233.34
_chemical_melting_point          398.5(5)
_chemical_name_systematic        'cyanodecalin 151'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-07-26
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2023-11-25 deposited with the CCDC.	2024-02-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.3680(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.25850(10)
_cell_length_b                   13.8145(2)
_cell_length_c                   10.04020(10)
_cell_measurement_reflns_used    11134
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.3790
_cell_measurement_theta_min      4.5120
_cell_volume                     1357.99(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.945
_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    103.00 177.00   0.50    0.08    --  108.01 125.00 150.00  148
  2  \w    143.00 169.00   0.50    0.08    --  108.01  24.00-114.00   52
  3  \w     87.00 133.00   0.50    0.08    --  108.01  24.00-114.00   92
  4  \w     16.00  62.00   0.50    0.05    --   43.18  24.00-114.00   92
  5  \w   -108.00 -82.00   0.50    0.05    --  -43.18 -24.00  81.00   52
  6  \w   -117.00 -81.00   0.50    0.05    --  -43.18 -77.00   0.00   72
  7  \w    -72.00 -18.00   0.50    0.05    --  -43.18 -77.00   0.00  108
  8  \w    -58.00 -19.00   0.50    0.05    --  -43.18 -77.00 -60.00   78
  9  \w   -116.00 -64.00   0.50    0.05    --  -43.18 -77.00 -60.00  104
 10  \w   -114.00 -69.00   0.50    0.05    --  -43.18 -57.00 -90.00   90
 11  \w    -51.00 -26.00   0.50    0.05    --  -43.18 -57.00 -90.00   50
 12  \w    -84.00 -21.00   0.50    0.05    --  -43.18 -38.00   0.00  126
 13  \w    -42.00 -17.00   0.50    0.05    --  -43.18 -24.00  81.00   50
 14  \w    -79.00 -17.00   0.50    0.05    --  -43.18 125.00 -60.00  124
 15  \w    -73.00 -48.00   0.50    0.08    --  -96.00  61.00  30.00   50
 16  \w    -73.00 -23.00   0.50    0.08    --  -96.00  61.00 150.00  100
 17  \w    -71.00 -22.00   0.50    0.08    --  -96.00  61.00   0.00   98
 18  \w    -67.00 -26.00   0.50    0.08    --  -96.00  61.00 -30.00   82
 19  \w    -49.00 -22.00   0.50    0.08    --  -96.00  45.00 -60.00   54
 20  \w    -19.00   6.00   0.50    0.05    --  -43.18  24.00-114.00   50
 21  \w    -64.00 -23.00   0.50    0.08    --  -96.00   0.00 -60.00   82
 22  \w    -92.00 -67.00   0.50    0.08    --  -96.00 -77.00  30.00   50
 23  \w    -93.00 -67.00   0.50    0.08    --  -96.00 -77.00 -14.53   52
 24  \w    -93.00 -67.00   0.50    0.08    --  -96.00 -77.00 -30.00   52
 25  \w    -92.00 -67.00   0.50    0.08    --  -96.00 -77.00   0.00   50
 26  \w    -94.00 -68.00   0.50    0.08    --  -96.00 -77.00  60.00   52
 27  \w    -92.00 -67.00   0.50    0.08    --  -96.00 -76.00  49.23   50
 28  \w    -94.00 -69.00   0.50    0.08    --  -96.00 -75.00  42.76   50
 29  \w   -170.00-100.00   0.50    0.08    --  -96.00 -77.00  30.00  140
 30  \w   -129.00-104.00   0.50    0.08    --  -96.00 -76.00 -35.02   50
 31  \w    -95.00 -70.00   0.50    0.08    --  -96.00 -73.00 -44.15   50
 32  \w    -94.00 -67.00   0.50    0.08    --  -96.00 -76.00 -35.02   54
 33  \w    -96.00 -70.00   0.50    0.08    --  -96.00 -75.00 -22.70   52
 34  \w    -95.00 -69.00   0.50    0.08    --  -96.00 -73.00  -1.78   52
 35  \w    -95.00 -69.00   0.50    0.08    --  -96.00 -75.00   9.83   52
 36  \w    -94.00 -69.00   0.50    0.08    --  -96.00 -71.00  12.74   50
 37  \w   -100.00 -75.00   0.50    0.08    --  -96.00 -61.00  60.00   50
 38  \w   -147.00-120.00   0.50    0.08    --  -96.00 -71.00  12.74   54
 39  \w   -167.00-141.00   0.50    0.08    --  -96.00 -61.00  60.00   52
 40  \w   -170.00 -70.00   0.50    0.08    --  -96.00 -72.00 -48.95  200
 41  \w   -169.00 -71.00   0.50    0.08    --  -96.00 -66.00 -70.32  196
 42  \w   -166.00-103.00   0.50    0.08    --  -96.00 -61.00 -30.00  126
 43  \w    -97.00 -72.00   0.50    0.08    --  -96.00 -61.00 -30.00   50
 44  \w   -104.00 -79.00   0.50    0.08    --  -96.00 -45.00   0.00   50
 45  \w   -166.00 -75.00   0.50    0.08    --  -96.00 -56.00  42.12  182
 46  \w   -123.00 -80.00   0.50    0.08    --  -96.00 -24.00  81.00   86
 47  \w    -30.00  23.00   0.50    0.05    --   43.18 -24.00  81.00  106
 48  \w     37.00  73.00   0.50    0.08    --  108.01 -61.00 120.00   72
 49  \w     37.00  80.00   0.50    0.08    --  108.01-125.00  90.00   86
 50  \w     36.00  86.00   0.50    0.05    --   43.18-125.00 -30.00  100
 51  \w     61.00 102.00   0.50    0.08    --  108.01 -95.00 -30.00   82
 52  \w     34.00  71.00   0.50    0.08    --  108.01 -61.00-180.00   74
;
_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      -0.0640436000
_diffrn_orient_matrix_UB_12      -0.0333669000
_diffrn_orient_matrix_UB_13      0.1129035000
_diffrn_orient_matrix_UB_21      -0.1435693000
_diffrn_orient_matrix_UB_22      0.0096533000
_diffrn_orient_matrix_UB_23      -0.1052045000
_diffrn_orient_matrix_UB_31      0.0071500000
_diffrn_orient_matrix_UB_32      -0.1059418000
_diffrn_orient_matrix_UB_33      -0.0451209000
_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  0.0372
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            17558
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.769
_diffrn_reflns_theta_min         4.516
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.542
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.316
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.141
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: n-hexane-ethyl acetate'
_exptl_crystal_size_max          0.498
_exptl_crystal_size_mid          0.223
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2635
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0374
_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^)+(0.0573P)^2^+0.3372P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1051
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2468
_reflns_number_total             2635
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00088a2.cif
_cod_data_source_block           exp_151_auto
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '398-399' was changed to
'398.5(5)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7159796--7159798.cif.
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7159796
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'C15 H23 N O'
_shelx_estimated_absorpt_t_max   0.909
_shelx_estimated_absorpt_t_min   0.773
_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 Ternary CH refined with riding coordinates:
 C005(H005), C006(H006), C007(H007), C008(H008)
2.b Secondary CH2 refined with riding coordinates:
 C00A(H00A,H00B), C00B(H00C,H00D), C00C(H00E,H00F), C00E(H00J,H00K), C00G(H00O,
 H00P)
2.c Idealised Me refined as rotating group:
 C00D(H00G,H00H,H00I), C00F(H00L,H00M,H00N), C00H(H00Q,H00R,H00S)
;
_shelx_res_checksum              40686
_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 0.782