Enantioselective Total Synthesis of (-)-Pavidolide B.
Zhang, Peng-Peng; Yan, Zhi-Ming; Li, Yuan-He; Gong, Jian-Xian; Yang, Zhen; Journal of the American Chemical Society 139 (2017) 13989–13992; doi:10.1021/jacs.7b07388

data_4131602
_publ_section_title
;
 Enantioselective Total Synthesis of (-)-Pavidolide B.
;
_journal_issue                   40
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13989
_journal_page_last               13992
_journal_paper_doi               10.1021/jacs.7b07388
_journal_volume                  139
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H26 O4'
_chemical_formula_sum            'C20 H26 O4'
_chemical_formula_weight         330.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-06-22
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.2361(15)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.40913(14)
_cell_length_b                   5.77298(8)
_cell_length_c                   15.8083(2)
_cell_measurement_reflns_used    7361
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.4970
_cell_measurement_theta_min      5.2590
_cell_volume                     855.10(2)
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_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 0.991
_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   -117.00 -14.00   1.00    1.00    --  -40.46 -37.00-180.00  103
  2  \w   -117.00 -14.00   1.00    1.00    --  -40.46 -37.00  90.00  103
  3  \w    -36.00  67.00   1.00    1.00    --   40.46 -37.00 -30.00  103
  4  \w     23.00  98.00   1.00    1.00    --   40.46-125.00-150.00   75
  5  \w      1.00  82.00   1.00    1.00    --   40.46 -99.00 -30.00   81
  6  \w     77.00 178.00   1.00    1.00    --  107.48  61.00 150.00  101
  7  \w     33.00 137.00   1.00    1.00    --  107.48 -58.00 -39.00  104
  8  \w     74.00 178.00   1.00    1.00    --  107.48  77.00-180.00  104
  9  \w     23.00 109.00   1.00    1.00    --  107.48 -94.00 -60.00   86
 10  \w     77.00 178.00   1.00    1.00    --  107.48  61.00  30.00  101
 11  \w     74.00 178.00   1.00    1.00    --  107.48  77.00 150.00  104
 12  \w     77.00 178.00   1.00    1.00    --  107.48  61.00-180.00  101
 13  \w    100.00 178.00   1.00    1.00    --  107.48 111.00  30.00   78
 14  \w     77.00 178.00   1.00    1.00    --  107.48  61.00-150.00  101
 15  \w     77.00 178.00   1.00    1.00    --  107.48  61.00-120.00  101
 16  \w     80.00 178.00   1.00    1.00    --  107.48  45.00-120.00   98
 17  \w     78.00 178.00   1.00    1.00    --  107.48  58.00 101.00  100
 18  \w     80.00 178.00   1.00    1.00    --  107.48  45.00-150.00   98
 19  \w     77.00 178.00   1.00    1.00    --  107.48  30.00-120.00  101
 20  \w     23.00 109.00   1.00    1.00    --  107.48 -94.00-120.00   86
 21  \w    -96.00 -41.00   1.00    1.00    --  -40.46 125.00  60.00   55
;
_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      -0.0637924000
_diffrn_orient_matrix_UB_12      0.1563333000
_diffrn_orient_matrix_UB_13      -0.0728077000
_diffrn_orient_matrix_UB_21      0.1498699000
_diffrn_orient_matrix_UB_22      0.0954296000
_diffrn_orient_matrix_UB_23      -0.0116243000
_diffrn_orient_matrix_UB_31      0.0223426000
_diffrn_orient_matrix_UB_32      -0.1941800000
_diffrn_orient_matrix_UB_33      -0.0643131000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10343
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.651
_diffrn_reflns_theta_min         4.719
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.709
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62566
_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            colorless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 1418 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.11(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3372
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0293
_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^)+(0.0445P)^2^+0.1210P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0767
_refine_ls_wR_factor_ref         0.0774
_reflns_Friedel_coverage         0.788
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.962
_reflns_number_gt                3293
_reflns_number_total             3372
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b07388_si_003.cif
_cod_data_source_block           exp_679
_cod_database_code               4131602
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.926
_shelx_estimated_absorpt_t_min   0.895
_reflns_odcompleteness_completeness 99.94
_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 Ternary CH refined with riding coordinates:
 C1(H1), C11(H11), C15(H15), C13(H13), C14(H14), C12(H12), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C6(H6A,H6B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C16(H16A,H16B,
 H16C)
;
_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 1.944
_oxdiff_exptl_absorpt_empirical_full_min 0.640