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_7159797
_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 H25 N'
_chemical_formula_sum            'C16 H25 N'
_chemical_formula_weight         231.37
_chemical_melting_point          406.5(5)
_chemical_name_systematic        'halichonadin C'
_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             2023-07-20
_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                 100.166(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5724(2)
_cell_length_b                   19.8160(4)
_cell_length_c                   7.59510(10)
_cell_measurement_reflns_used    5010
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.0330
_cell_measurement_theta_min      4.4710
_cell_volume                     1418.07(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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.946
_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    -51.00 -22.00   0.50    0.21    --  -96.00  45.00 120.00   58
  2  \w    -50.00 -23.00   0.50    0.21    --  -96.00  45.00   0.00   54
  3  \w    -63.00 -30.00   0.50    0.21    --  -96.00  61.00 -30.00   66
  4  \w    -50.00 -21.00   0.50    0.21    --  -96.00  45.00 -60.00   58
  5  \w    -49.00 -22.00   0.50    0.21    --  -96.00  45.00 -90.00   54
  6  \w    -49.00 -24.00   0.50    0.21    --  -96.00  45.00-180.00   50
  7  \w    -47.00 -21.00   0.50    0.21    --  -96.00  45.00  30.00   52
  8  \w    -49.00 -23.00   0.50    0.21    --  -96.00  45.00  90.00   52
  9  \w    -70.00 -45.00   0.50    0.05    --  -42.99 117.00 160.00   50
 10  \w    -69.00 -32.00   0.50    0.21    --  -96.00 164.00 -50.00   74
 11  \w    -97.00 -72.00   0.50    0.05    --  -42.99 164.00 -50.00   50
 12  \w   -148.00-122.00   0.50    0.21    --  -96.00-117.00  73.00   52
 13  \w   -114.00 -83.00   0.50    0.05    --  -42.99-164.00 -75.00   62
 14  \w    -77.00 -48.00   0.50    0.05    --  -42.99-164.00 -75.00   58
 15  \w   -116.00 -22.00   0.50    0.05    --  -42.99 -57.00 -30.00  188
 16  \w    127.00 178.00   0.50    0.21    --  108.01  30.00 -30.00  102
 17  \w     88.00 113.00   0.50    0.21    --  108.01 164.00 -50.00   50
 18  \w     84.00 114.00   0.50    0.21    --  108.01  30.00 -30.00   60
 19  \w     38.00  68.00   0.50    0.21    --  108.01 -61.00-150.00   60
 20  \w     45.00  70.00   0.50    0.21    --  108.01 -61.00-120.00   50
 21  \w    -33.00  32.00   0.50    0.05    --   42.99 -19.00 120.00  130
 22  \w     71.00  99.00   0.50    0.21    --  108.01 -77.00  90.00   56
 23  \w     42.00  68.00   0.50    0.21    --  108.01 -77.00  90.00   52
 24  \w     34.00  60.00   0.50    0.21    --  108.01 -61.00  90.00   52
 25  \w     50.00  76.00   0.50    0.21    --  108.01 -95.00  90.00   52
 26  \w     37.00 106.00   0.50    0.21    --  108.01-117.00  73.00  138
 27  \w     59.00  84.00   0.50    0.05    --   42.99-117.00  73.00   50
 28  \w     81.00 106.00   0.50    0.21    --  108.01 -95.00  90.00   50
 29  \w     63.00 109.00   0.50    0.05    --   42.99-164.00 -75.00   92
 30  \w     96.00 133.00   0.50    0.21    --  108.01-164.00 -75.00   74
 31  \w     54.00  87.00   0.50    0.21    --  108.01-164.00 -75.00   66
;
_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      -0.1346032000
_diffrn_orient_matrix_UB_12      0.0347068000
_diffrn_orient_matrix_UB_13      -0.1013232000
_diffrn_orient_matrix_UB_21      -0.0770484000
_diffrn_orient_matrix_UB_22      -0.0685802000
_diffrn_orient_matrix_UB_23      -0.0210609000
_diffrn_orient_matrix_UB_31      -0.0520283000
_diffrn_orient_matrix_UB_32      0.0115686000
_diffrn_orient_matrix_UB_33      0.1781803000
_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  0.0363
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            9021
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.070
_diffrn_reflns_theta_min         4.463
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.459
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.312
_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    1.084
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: n-hexane-dichloromethane'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2768
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0429
_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^)+(0.0514P)^2^+0.3504P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1137
_refine_ls_wR_factor_ref         0.1179
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2441
_reflns_number_total             2768
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00088a2.cif
_cod_data_source_block           exp_329_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/c
_cod_database_code               7159797
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C16H25N
_shelx_estimated_absorpt_t_max   0.964
_shelx_estimated_absorpt_t_min   0.856
_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:
 C002(H002), C003(H003), C004(H004), C007(H007)
2.b Secondary CH2 refined with riding coordinates:
 C008(H00A,H00B), C00B(H00I,H00J), C00D(H00M,H00N), C00E(H00O,H00P), C00F(H00Q,
 H00R)
2.c X=CH2 refined with riding coordinates:
 C00C(H00K,H00L)
2.d Idealised Me refined as rotating group:
 C009(H00C,H00D,H00E), C00A(H00F,H00G,H00H), C00G(H00S,H00T,H00U)
;
_shelx_res_checksum              24028
_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 1.298
_oxdiff_exptl_absorpt_empirical_full_min 0.738