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_7159798
_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         'C16 H27 N O'
_chemical_formula_sum            'C16 H27 N O'
_chemical_formula_weight         249.38
_chemical_melting_point          406.5(5)
_chemical_name_systematic        'methyldecalin 197'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 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                 99.765(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.89130(10)
_cell_length_b                   26.1001(4)
_cell_length_c                   9.5853(2)
_cell_measurement_reflns_used    9453
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.7190
_cell_measurement_theta_min      3.4270
_cell_volume                     1452.52(5)
_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_environment      N~2~
_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 0.942
_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    153.00 178.00   0.50    0.08    --  108.01 125.00 150.00   50
  2  \w     95.00 125.00   0.50    0.08    --  108.01 125.00 150.00   60
  3  \w     86.00 140.00   0.50    0.08    --  108.01  55.00 -63.00  108
  4  \w     41.00  67.00   0.50    0.05    --   42.99  55.00 -63.00   52
  5  \w     68.00  94.00   0.50    0.05    --   42.99  55.00 -63.00   52
  6  \w     70.00 100.00   0.50    0.08    --  108.01 -77.00 150.00   60
  7  \w     36.00  62.00   0.50    0.08    --  108.01 -55.00 152.00   52
  8  \w     36.00  65.00   0.50    0.08    --  108.01 -61.00  60.00   58
  9  \w     39.00  71.00   0.50    0.08    --  108.01 -61.00   0.00   64
 10  \w     48.00 105.00   0.50    0.08    --  108.01 -95.00 -90.00  114
 11  \w     77.00 112.00   0.50    0.08    --  108.01-125.00 -60.00   70
 12  \w     41.00  67.00   0.50    0.08    --  108.01-125.00 -60.00   52
 13  \w     34.00  94.00   0.50    0.05    --   42.99-125.00   0.00  120
 14  \w    -31.00  -2.00   0.50    0.05    --   42.99 -38.00-120.00   58
 15  \w      8.00  42.00   0.50    0.05    --   42.99 -38.00-120.00   68
 16  \w   -115.00 -26.00   0.50    0.05    --  -42.99 -57.00  90.00  178
 17  \w   -114.00 -22.00   0.50    0.05    --  -42.99 -55.00 152.00  184
 18  \w      0.00  26.00   0.50    0.05    --   42.99 -55.00 152.00   52
 19  \w   -119.00 -23.00   0.50    0.05    --  -42.99 -38.00   0.00  192
 20  \w   -119.00 -70.00   0.50    0.05    --  -42.99 -38.00 -30.00   98
 21  \w   -102.00 -67.00   0.50    0.08    --  -96.00 -77.00  60.00   70
 22  \w    -97.00 -72.00   0.50    0.08    --  -96.00 -61.00  60.00   50
 23  \w   -164.00 -67.00   0.50    0.08    --  -96.00 -77.00  30.00  194
 24  \w   -163.00-113.00   0.50    0.08    --  -96.00 -61.00  60.00  100
 25  \w    -94.00 -69.00   0.50    0.08    --  -96.00 -77.00  90.00   50
 26  \w   -131.00 -78.00   0.50    0.08    --  -96.00 -55.00 152.00  106
 27  \w   -108.00 -78.00   0.50    0.08    --  -96.00 -45.00  90.00   60
 28  \w   -104.00 -76.00   0.50    0.08    --  -96.00 -45.00  60.00   56
 29  \w   -121.00 -75.00   0.50    0.08    --  -96.00 -45.00  30.00   92
 30  \w   -152.00-125.00   0.50    0.08    --  -96.00 -45.00  60.00   54
 31  \w   -174.00-100.00   0.50    0.08    --  -96.00 -30.00   0.00  148
 32  \w    -47.00 -20.00   0.50    0.08    --  -96.00  45.00 -30.00   54
 33  \w    -62.00 -27.00   0.50    0.08    --  -96.00  55.00 -63.00   70
 34  \w    -69.00 -22.00   0.50    0.08    --  -96.00  61.00 -30.00   94
 35  \w    -51.00 -20.00   0.50    0.08    --  -96.00  45.00-120.00   62
 36  \w    -40.00 -15.00   0.50    0.05    --  -42.99  55.00 -63.00   50
 37  \w    -46.00 -20.00   0.50    0.08    --  -96.00  45.00  60.00   52
 38  \w    -51.00 -25.00   0.50    0.08    --  -96.00  45.00  90.00   52
 39  \w    -51.00 -26.00   0.50    0.08    --  -96.00  45.00 120.00   50
 40  \w    -59.00 -22.00   0.50    0.08    --  -96.00  61.00 150.00   74
 41  \w    -48.00 -22.00   0.50    0.08    --  -96.00  45.00 150.00   52
 42  \w   -171.00 -84.00   0.50    0.08    --  -96.00 -95.00 120.00  174
 43  \w   -167.00-141.00   0.50    0.08    --  -96.00 -95.00-120.00   52
 44  \w   -130.00 -88.00   0.50    0.08    --  -96.00 -95.00-120.00   84
;
_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      -0.2138135000
_diffrn_orient_matrix_UB_12      -0.0278765000
_diffrn_orient_matrix_UB_13      0.0351019000
_diffrn_orient_matrix_UB_21      -0.0325701000
_diffrn_orient_matrix_UB_22      -0.0269809000
_diffrn_orient_matrix_UB_23      -0.1450147000
_diffrn_orient_matrix_UB_31      0.1535481000
_diffrn_orient_matrix_UB_32      -0.0445117000
_diffrn_orient_matrix_UB_33      0.0658336000
_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  0.0337
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16600
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.180
_diffrn_reflns_theta_min         3.387
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.532
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.561
_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    1.140
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: n-hexane-ethyl acetate'
_exptl_crystal_size_max          0.257
_exptl_crystal_size_mid          0.187
_exptl_crystal_size_min          0.149
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2821
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0379
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0490P)^2^+0.4459P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0998
_refine_ls_wR_factor_ref         0.1021
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2610
_reflns_number_total             2821
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00088a2.cif
_cod_data_source_block           exp_197_auto
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '406-407' was changed to
'406.5(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/n
_cod_database_code               7159798
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'C16 H27 N O'
_shelx_estimated_absorpt_t_max   0.924
_shelx_estimated_absorpt_t_min   0.874
_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:
 C003(H003), C004(H004), C005(H005), C00E(H00M)
2.b Secondary CH2 refined with riding coordinates:
 C009(H00A,H00B), C00A(H00C,H00D), C00D(H00K,H00L), C00F(H00N,H00O), C00G(H00P,
 H00Q)
2.c Idealised Me refined as rotating group:
 C00B(H00E,H00F,H00G), C00C(H00H,H00I,H00J), C00H(H00R,H00S,H00T), C00I(H00U,
 H00V,H00W)
2.d Idealised tetrahedral OH refined as rotating group:
 O001(H001)
;
_shelx_res_checksum              12764
_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 1.290
_oxdiff_exptl_absorpt_empirical_full_min 0.813