Expediently Scalable Synthesis and Antifungal Exploration of (+)-Yahazunol and Related Meroterpenoids.
Zhang, Shasha; Wang, Xia; Hao, Jin; Li, Dangdang; Csuk, René; Li, Shengkun; Journal of natural products 81 (2018) 2010–2017; doi:10.1021/acs.jnatprod.8b00310

data_1553376
_publ_section_title
;
 Expediently Scalable Synthesis and Antifungal Exploration of
 (+)-Yahazunol and Related Meroterpenoids.
;
_journal_issue                   9
_journal_name_full               'Journal of natural products'
_journal_page_first              2010
_journal_page_last               2017
_journal_paper_doi               10.1021/acs.jnatprod.8b00310
_journal_volume                  81
_journal_year                    2018
_chemical_absolute_configuration ukn
_chemical_formula_moiety         'C21 H32 O3'
_chemical_formula_sum            'C21 H32 O3'
_chemical_formula_weight         332.46
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-09-28
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                100.197(3)
_cell_angle_beta                 100.924(3)
_cell_angle_gamma                91.722(3)
_cell_formula_units_Z            2
_cell_length_a                   6.2785(2)
_cell_length_b                   10.5538(4)
_cell_length_c                   14.3930(4)
_cell_measurement_reflns_used    6521
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.6490
_cell_measurement_theta_min      4.2580
_cell_volume                     919.64(5)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.994
_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    -17.00  22.00   0.50    0.50    --    0.00 -57.00  90.00   78
  2  \w    -54.00  12.00   0.50    0.50    --    0.00 -38.00-150.00  132
  3  \w    -63.00 -38.00   0.50    0.50    --    0.00 -57.00 -90.00   50
  4  \w    -66.00  11.00   0.50    0.50    --    0.00 -19.00-120.00  154
  5  \w    -33.00  -7.00   0.50    0.50    --    0.00 -38.00-180.00   52
  6  \w    -84.00 -37.00   0.50    0.50    --    0.00 -38.00-180.00   94
  7  \w     64.00 104.00   0.50    0.50    --   95.20 -82.00  90.00   80
  8  \w     34.00 126.00   0.50    0.50    --   95.20 -82.00 -60.00  184
  9  \w     11.00 119.00   0.50    0.50    --   95.20 -15.00 -60.00  216
 10  \w     86.00 126.00   0.50    0.50    --   95.20 -82.00   0.00   80
 11  \w     15.00 117.00   0.50    0.50    --   95.20 -82.00-180.00  204
 12  \w     10.00  37.00   0.50    0.50    --   95.20 -82.00  90.00   54
 13  \w     38.00  65.00   0.50    0.50    --   95.20 -82.00 150.00   54
 14  \w      8.00  34.00   0.50    0.50    --   95.20 -82.00-120.00   52
 15  \w      7.00 113.00   0.50    0.50    --   95.20 -61.00 -60.00  212
 16  \w     93.00 119.00   0.50    0.50    --   95.20 -82.00-120.00   52
 17  \w     80.00 159.00   0.50    0.50    --   95.20  30.00 -90.00  158
 18  \w     14.00  87.00   0.50    0.50    --   95.20 -30.00  60.00  146
 19  \w      6.00  32.00   0.50    0.50    --   95.20 -82.00 150.00   52
 20  \w     84.00 170.00   0.50    0.50    --   95.20  30.00 -60.00  172
 21  \w     57.00 105.00   0.50    0.50    --   95.20 -82.00  30.00   96
 22  \w     14.00 101.00   0.50    0.50    --   95.20 -61.00-180.00  174
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0701448000
_diffrn_orient_matrix_UB_12      0.0652275000
_diffrn_orient_matrix_UB_13      0.1065923000
_diffrn_orient_matrix_UB_21      0.0048978000
_diffrn_orient_matrix_UB_22      0.1330589000
_diffrn_orient_matrix_UB_23      -0.0298385000
_diffrn_orient_matrix_UB_31      -0.2403675000
_diffrn_orient_matrix_UB_32      0.0115548000
_diffrn_orient_matrix_UB_33      0.0076047000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8796
_diffrn_reflns_point_group_measured_fraction_full 0.616
_diffrn_reflns_point_group_measured_fraction_max 0.592
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.952
_diffrn_reflns_theta_min         3.183
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.613
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81133
_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            colorless
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     447
_refine_ls_number_reflns         4408
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0359
_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^)+(0.0570P)^2^+0.3790P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1077
_reflns_Friedel_coverage         0.226
_reflns_Friedel_fraction_full    0.237
_reflns_Friedel_fraction_max     0.218
_reflns_number_gt                4226
_reflns_number_total             4408
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np8b00310_si_001.cif
_cod_data_source_block           zsl-45
_cod_database_code               1553376
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.936
_shelx_estimated_absorpt_t_min   0.908
_reflns_odcompleteness_completeness 99.48
_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:
 C8(H8), C00I(H00I), C12(H12), C00X(H00X)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7a,H7b), C00D(H00d,H00e), C10(H10a,H10b), C14(H14a,H14b), C00Y(H00j,H00k),
  C16(H16a,H16b), C11(H11a,H11b), C016(H01a,H01b), C017(H01c,H01d), C019(H01h,
 H01i), C15(H15a,H15b), C01B(H01j,H01k)
2.c Aromatic/amide H refined with riding coordinates:
 C00M(H00M), C00N(H00N), C5(H5), C2(H2a), C3(H3a), C014(H014)
2.d Idealised Me refined as rotating group:
 C00J(H00a,H00b,H00c), C00Q(H00f,H00g,H00h), C20(H20a,H20b,H20c), C00Z(H00l,
 H00o,H00p), C18(H18a,H18b,H18c), C19(H19a,H19b,H19c), C018(H01e,H01f,H01g),
 C01C(H01l,H01m,H01n)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O002(H002), O1(H1), O004(H004), O2(H2), O006(H006)
;
_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 3.526
_oxdiff_exptl_absorpt_empirical_full_min 0.641