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_4127797
_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 H30 O2'
_chemical_formula_sum            'C15 H30 O2'
_chemical_formula_weight         242.39
_space_group_crystal_system      hexagonal
_space_group_IT_number           173
_space_group_name_Hall           'P 6c'
_space_group_name_H-M_alt        'P 63'
_symmetry_space_group_name_Hall  'P 6c'
_symmetry_space_group_name_H-M   'P 63'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-06-15
_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                120
_cell_formula_units_Z            18
_cell_length_a                   28.5768(2)
_cell_length_b                   28.5768(2)
_cell_length_c                   9.68441(9)
_cell_measurement_reflns_used    26415
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.7810
_cell_measurement_theta_min      1.6840
_cell_volume                     6849.06(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.6a (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      100
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.982
_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    -80.00  22.00   1.00    1.00    --    0.00  60.00   0.00  102
  2  \w   -135.00 -15.00   1.00    1.00    --  -45.00  60.00 180.00  120
  3  \w   -135.00  30.00   1.00    1.00    --  -45.00  60.00 240.00  165
  4  \w   -174.00 -16.00   1.00    5.00    --  -90.00  60.00 180.00  158
  5  \w   -180.00 -40.00   1.00    5.00    --  -90.00  20.00 180.00  140
  6  \w   -180.00 -60.00   1.00    5.00    --  -90.00  60.00 120.00  120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0537993000
_diffrn_orient_matrix_UB_12      -0.0540024000
_diffrn_orient_matrix_UB_13      -0.0006413000
_diffrn_orient_matrix_UB_21      0.0312629000
_diffrn_orient_matrix_UB_22      -0.0308775000
_diffrn_orient_matrix_UB_23      0.0093908000
_diffrn_orient_matrix_UB_31      -0.0020417000
_diffrn_orient_matrix_UB_32      0.0016630000
_diffrn_orient_matrix_UB_33      0.1588100000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            39625
_diffrn_reflns_point_group_measured_fraction_full 0.863
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.799
_diffrn_reflns_theta_min         1.785
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.519
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59717
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.6a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.058
_exptl_crystal_description       block
_exptl_crystal_F_000             2448
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 2439 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     478
_refine_ls_number_reflns         7215
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0437
_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^)+(0.0550P)^2^+3.7880P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_ref         0.1230
_reflns_Friedel_coverage         0.631
_reflns_Friedel_fraction_full    0.718
_reflns_Friedel_fraction_max     0.704
_reflns_number_gt                6901
_reflns_number_total             7215
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b00621_si_006.cif
_cod_data_source_block           yxr-12-6
_cod_depositor_comments
;

2020-08-12
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        6849.08(12)
_cod_original_formula_moiety     '3(C15 H30 O2)'
_cod_original_formula_sum        'C45 H90 O6'
_cod_original_formula_units_Z    6
_cod_original_formula_weight     727.16
_cod_database_code               4127797
_reflns_odcompleteness_completeness 98.36
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.68
_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:
 C1(H1A), C3(H3), C6(H6), C7(H7), C10(H10), C12(H12), C1"(H1"A), C3"(H3"),
 C6"(H6"), C7"(H7"), C10"(H10"), C12"(H12"), C1'(H1'A), C3'(H3'), C6'(H6'),
 C7'(H7'), C10'(H10'), C12'(H12')
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C5(H5A,H5B), C8(H8A,H8B), C9(H9A,H9B), C2"(H2"A,
 H2"B), C4"(H4"A,H4"B), C5"(H5"A,H5"B), C8"(H8"A,H8"B), C9"(H9"A,H9"B),
 C2'(H2'A,H2'B), C4'(H4'A,H4'B), C5'(H5'A,H5'B), C8'(H8'A,H8'B), C9'(H9'A,H9'B)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C), C11"(H11D,H11E,H11F), C13"(H13D,H13E,H13F), C14"(H14D,H14E,H14F),
 C15"(H15D,H15E,H15F), C11'(H11G,H11H,H11I), C13'(H13G,H13H,H13I), C14'(H14G,
 H14H,H14I), C15'(H15G,H15H,H15I)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O1"(H1"), O2"(H2"), O1'(H1'), O2'(H2')
;
_shelx_res_checksum              47489
_shelx_hkl_checksum              64580
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.386
_oxdiff_exptl_absorpt_empirical_full_min 0.624