Scalable Total Synthesis of (-)-Vinigrol.
Yu, Xuerong; Xiao, Lianghong; Wang, Zechun; Luo, Tuoping; Journal of the American Chemical Society 141 (2019) 3440–3443; doi:10.1021/jacs.9b00621

data_4127799
_publ_section_title
;
 Scalable Total Synthesis of (-)-Vinigrol.
;
_journal_issue                   8
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3440
_journal_page_last               3443
_journal_paper_doi               10.1021/jacs.9b00621
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C15 H28 O'
_chemical_formula_sum            'C15 H28 O'
_chemical_formula_weight         224.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-11-06
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   5.29465(6)
_cell_length_b                   19.8691(2)
_cell_length_c                   39.0839(4)
_cell_measurement_reflns_used    10021
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.7840
_cell_measurement_theta_min      4.0470
_cell_volume                     4111.62(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.979
_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    -24.00   1.00   1.00    6.08    --    0.00  15.00  49.00   25
  2  \w   -108.00 -57.00   1.00   24.30    --  -90.00  15.00  49.00   51
  3  \w    -75.00  12.00   1.00    6.08    --    0.00  55.00-180.00   87
  4  \w   -152.00-126.00   1.00   24.30    --  -90.00  29.00-120.00   26
  5  \w    -26.00  -1.00   1.00   24.30    --  -90.00  29.00-120.00   25
  6  \w   -179.00-153.00   1.00   24.30    --  -90.00  29.00-120.00   26
  7  \w   -137.00-110.00   1.00   24.30    --  -90.00  43.00  60.00   27
  8  \w    -53.00  -3.00   1.00   24.30    --  -90.00  43.00  60.00   50
  9  \w   -178.00  -2.00   1.00   24.30    --  -90.00  55.00-120.00  176
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0575648000
_diffrn_orient_matrix_UB_12      0.0189409000
_diffrn_orient_matrix_UB_13      0.0374065000
_diffrn_orient_matrix_UB_21      0.0453918000
_diffrn_orient_matrix_UB_22      -0.0735296000
_diffrn_orient_matrix_UB_23      0.0109024000
_diffrn_orient_matrix_UB_31      0.2815976000
_diffrn_orient_matrix_UB_32      0.0157727000
_diffrn_orient_matrix_UB_33      0.0058912000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0789
_diffrn_reflns_av_unetI/netI     0.0737
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            14636
_diffrn_reflns_point_group_measured_fraction_full 0.939
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.310
_diffrn_reflns_theta_min         4.058
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.488
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.12061
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light colourless'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.087
_exptl_crystal_description       needle
_exptl_crystal_F_000             1512
_exptl_crystal_size_max          0.72
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details
;
 Flack x determined using 2006 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     448
_refine_ls_number_reflns         7103
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.1002
_refine_ls_R_factor_gt           0.0796
_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^)+(0.1290P)^2^+4.4410P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2066
_refine_ls_wR_factor_ref         0.2303
_reflns_Friedel_coverage         0.624
_reflns_Friedel_fraction_full    0.869
_reflns_Friedel_fraction_max     0.841
_reflns_number_gt                6339
_reflns_number_total             7103
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b00621_si_004.cif
_cod_data_source_block           yxr-13-42a
_cod_depositor_comments
;

2020-06-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '3(C15 H28 O)'
_cod_original_formula_sum        'C45 H84 O3'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     673.12
_cod_database_code               4127799
_reflns_odcompleteness_completeness 99.26
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C1A(H1AA), C2A(H2A), C9A(H9A), C13A(H13A), C1B(H1BA), C2B(H2B), C9B(H9B),
 C13B(H13B), C1C(H1CA), C2C(H2C), C9C(H9C), C13C(H13C)
2.b Secondary CH2 refined with riding coordinates:
 C3A(H3AA,H3AB), C4A(H4AA,H4AB), C7A(H7AA,H7AB), C8A(H8AA,H8AB), C10A(H10E,
 H10F), C3B(H3BA,H3BB), C4B(H4BA,H4BB), C7B(H7BA,H7BB), C8B(H8BA,H8BB),
 C10B(H10C,H10D), C3C(H3CA,H3CB), C4C(H4CA,H4CB), C7C(H7CA,H7CB), C8C(H8CA,
 H8CB), C10C(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C5A(H5A), C5B(H5B), C5C(H5C)
2.d Idealised Me refined as rotating group:
 C11A(H11G,H11H,H11I), C12A(H12G,H12H,H12I), C14A(H14G,H14H,H14I), C15A(H15G,
 H15H,H15I), C11B(H11D,H11E,H11F), C12B(H12D,H12E,H12F), C14B(H14D,H14E,H14F),
 C15B(H15D,H15E,H15F), C11C(H11A,H11B,H11C), C12C(H12A,H12B,H12C), C14C(H14A,
 H14B,H14C), C15C(H15A,H15B,H15C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1A(H1A), O1B(H1B), O1C(H1C)
;
_shelx_res_checksum              16483
_shelx_hkl_checksum              68765
_shelx_shelxl_version_number     2014/7
_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 2.177
_oxdiff_exptl_absorpt_empirical_full_min 0.083