Asymmetric Total Synthesis of (+)-Waihoensene.
Qu, Yongzheng; Wang, Zheyuan; Zhang, Zhongchao; Zhang, Wendou; Huang, Jun; Yang, Zhen; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.0c02143

data_4134551
_publ_section_title
;
 Asymmetric Total Synthesis of (+)-Waihoensene.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c02143
_journal_year                    2020
_chemical_formula_moiety         'C19 H28 O3'
_chemical_formula_sum            'C19 H28 O3'
_chemical_formula_weight         304.41
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-08-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.200(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2573(3)
_cell_length_b                   11.5170(3)
_cell_length_c                   14.0879(3)
_cell_measurement_reflns_used    3704
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      73.4520
_cell_measurement_theta_min      3.7870
_cell_volume                     1598.17(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (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_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.966
_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      6.00  32.00   1.00    1.00    --  -40.98  57.00 -90.00   26
  2  \w     26.00  89.00   1.00    1.00    --   40.98-125.00 -60.00   63
  3  \w     35.00 126.00   1.00    1.00    --  106.95 -45.00 -90.00   91
  4  \w     80.00 105.00   1.00    1.00    --  106.95  30.00-150.00   25
  5  \w    109.00 158.00   1.00    1.00    --  106.95  30.00-150.00   49
  6  \w     80.00 178.00   1.00    1.00    --  106.95  61.00  60.00   98
  7  \w    138.00 166.00   1.00    1.00    --  106.95 125.00 150.00   28
  8  \w    144.00 169.00   1.00    1.00    --  106.95 125.00  90.00   25
  9  \w    104.00 131.00   1.00    1.00    --  106.95 125.00  90.00   27
 10  \w     51.00 150.00   1.00    1.00    --  106.95 -15.00  30.00   99
 11  \w     23.00  76.00   1.00    1.00    --   40.98-125.00  90.00   53
 12  \w   -108.00 -15.00   1.00    1.00    --  -40.98 -57.00 120.00   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0807165000
_diffrn_orient_matrix_UB_12      -0.1142544000
_diffrn_orient_matrix_UB_13      -0.0116194000
_diffrn_orient_matrix_UB_21      -0.0020369000
_diffrn_orient_matrix_UB_22      0.0077513000
_diffrn_orient_matrix_UB_23      0.1087606000
_diffrn_orient_matrix_UB_31      -0.1338280000
_diffrn_orient_matrix_UB_32      0.0692485000
_diffrn_orient_matrix_UB_33      -0.0317916000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6102
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.637
_diffrn_reflns_theta_min         4.759
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.660
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64474
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.265
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3129
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0471
_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^)+(0.0777P)^2^+0.4571P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1249
_refine_ls_wR_factor_ref         0.1283
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2878
_reflns_number_total             3129
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c02143_si_003.cif
_cod_data_source_block           qyz
_cod_original_cell_volume        1598.16(8)
_cod_database_code               4134551
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C15(H15A,H15B), C8(H8A,H8B), C14(H14A,H14B), C5(H5A,H5B),
 C19(H19A,H19B), C7(H7A,H7B), C3(H3A,H3B), C12(H12A,H12B), C4(H4A,H4B)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_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 1.488
_oxdiff_exptl_absorpt_empirical_full_min 0.623