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_4134552
_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_absolute_configuration ad
_chemical_formula_moiety         'C16 H20 O2'
_chemical_formula_sum            'C16 H20 O2'
_chemical_formula_weight         244.32
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-09-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.36180(10)
_cell_length_b                   12.5083(2)
_cell_length_c                   27.8448(4)
_cell_measurement_reflns_used    9180
_cell_measurement_temperature    108(12)
_cell_measurement_theta_max      73.4830
_cell_measurement_theta_min      3.1430
_cell_volume                     2564.05(7)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      108(12)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_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   -113.00 -13.00   1.00    1.00    --  -41.23 -57.00  90.00  100
  2  \w      1.00  82.00   1.00    1.00    --   41.23 -99.00 -60.00   81
  3  \w     17.00 116.00   1.00    1.00    --   41.23  37.00-180.00   99
  4  \w     34.00 133.00   1.00    1.69    --  106.95 -45.00 -60.00   99
  5  \w     31.00 135.00   1.00    1.69    --  106.95 -30.00-150.00  104
  6  \w     94.00 178.00   1.00    1.69    --  106.95 125.00-180.00   84
  7  \w     24.00 109.00   1.00    1.69    --  106.95 -94.00-150.00   85
  8  \w     94.00 178.00   1.00    1.69    --  106.95 125.00  60.00   84
  9  \w     35.00 136.00   1.00    1.69    --  106.95 -61.00-180.00  101
 10  \w   -117.00 -92.00   1.00    1.00    --  -41.23 -77.00 -30.00   25
;
_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      0.0447750000
_diffrn_orient_matrix_UB_12      -0.1122901000
_diffrn_orient_matrix_UB_13      0.0193683000
_diffrn_orient_matrix_UB_21      0.0289087000
_diffrn_orient_matrix_UB_22      0.0471601000
_diffrn_orient_matrix_UB_23      0.0505343000
_diffrn_orient_matrix_UB_31      -0.2023908000
_diffrn_orient_matrix_UB_32      -0.0181596000
_diffrn_orient_matrix_UB_33      0.0115208000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            13368
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.578
_diffrn_reflns_theta_min         3.174
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.643
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79480
_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    1.266
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.500
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 2015 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         5059
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0440
_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^)+(0.0596P)^2^+1.1307P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1173
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.972
_reflns_number_gt                4897
_reflns_number_total             5059
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c02143_si_002.cif
_cod_data_source_block           l-4-2
_cod_database_code               4134552
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.92
_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
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C3(H3A,H3B), C10(H10C,H10D), C14(H14C,H14D), C5(H5A,H5B), C7(H7A,
 H7B), C8(H8A,H8B), C15(H15C,H15D), C10B(H10A,H10B), C6B(H6BA,H6BB), C8B(H8BA,
 H8BB), C4B(H4BA,H4BB), C5B(H5BA,H5BB), C15B(H15A,H15B), C14B(H14A,H14B),
 C7B(H7BA,H7BB)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C12B(H12B)
2.c Idealised Me refined as rotating group:
 C16(H16D,H16E,H16F), C16B(H16A,H16B,H16C)
;
_shelx_res_checksum              85532
_shelx_hkl_checksum              74747
_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 1.326
_oxdiff_exptl_absorpt_empirical_full_min 0.696