Biomimetic total syntheses of baefrutones A-D, baeckenon B, and frutescones A, D-F.
Hou, Ji-Qin; Yu, Jiang-Hong; Zhao, Heng; Dong, Ying-Ying; Peng, Qiu-Shi; Zhang, Bao-Bao; Wang, Hao; Organic & biomolecular chemistry 18 (2020) 1135–1139; doi:10.1039/c9ob02490e

data_7157307
_publ_section_title
;
 Biomimetic total syntheses of baefrutones A-D, baeckenon B, and
 frutescones A, D-F.
;
_journal_issue                   6
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1135
_journal_page_last               1139
_journal_paper_doi               10.1039/c9ob02490e
_journal_volume                  18
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C35 H48 O7'
_chemical_formula_sum            'C35 H48 O7'
_chemical_formula_weight         580.73
_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             2019-10-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-10-30 deposited with the CCDC.	2020-01-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3336(2)
_cell_length_b                   16.1275(3)
_cell_length_c                   18.2549(3)
_cell_measurement_reflns_used    9765
_cell_measurement_temperature    299.99(10)
_cell_measurement_theta_max      75.9730
_cell_measurement_theta_min      3.6640
_cell_volume                     3336.68(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_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      air
_diffrn_ambient_temperature      299.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.964
_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     23.00 118.00   0.50    0.05    --   46.37  76.00 155.00  190
  2  \w   -168.00 -85.00   0.50    0.20    -- -100.00 -50.00 169.00  166
  3  \w   -123.00 -27.00   0.50    0.20    -- -100.00  76.00 155.00  192
  4  \w   -168.00 -88.00   0.50    0.20    -- -100.00-107.00 -56.00  160
  5  \w    -95.00 -20.00   0.50    0.05    --  -46.37 125.00 -60.00  150
  6  \w     73.00 118.00   0.50    0.05    --   46.37 125.00  90.00   90
  7  \w     73.00 118.00   0.50    0.05    --   46.37 125.00-180.00   90
  8  \w   -168.00 -84.00   0.50    0.20    -- -100.00 -94.00 150.00  168
  9  \w     93.00 169.00   0.50    0.20    --  107.75  45.00 -60.00  152
 10  \w     90.00 169.00   0.50    0.20    --  107.75  61.00  30.00  158
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Oxford CCD diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0048381000
_diffrn_orient_matrix_UB_12      -0.0259038000
_diffrn_orient_matrix_UB_13      -0.0811616000
_diffrn_orient_matrix_UB_21      0.1126114000
_diffrn_orient_matrix_UB_22      -0.0522139000
_diffrn_orient_matrix_UB_23      0.0104054000
_diffrn_orient_matrix_UB_31      -0.0760653000
_diffrn_orient_matrix_UB_32      -0.0757104000
_diffrn_orient_matrix_UB_33      0.0204349000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18117
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.558
_diffrn_reflns_theta_min         3.657
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.636
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84820
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.14a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_description       block
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Flack x determined using 1955 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(13)
_refine_ls_extinction_coef       0.0016(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     394
_refine_ls_number_reflns         6519
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0462
_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^)+(0.0898P)^2^+0.0401P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1338
_refine_ls_wR_factor_ref         0.1448
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_full    0.962
_reflns_Friedel_fraction_max     0.887
_reflns_number_gt                5311
_reflns_number_total             6519
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob02490e2.cif
_cod_data_source_block           njq-pm-8-300k
_cod_depositor_comments          'Adding full bibliography for 7157307.cif.'
_cod_original_cell_volume        3336.67(12)
_cod_database_code               7157307
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.847
_shelx_estimated_absorpt_t_min   0.822
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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. Restrained distances
 H16-H11
 2.2 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C11(H11), C22(H22), C24(H24), C27(H27), C29(H29), C33(H33)
3.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C23(H23A,H23B), C36(H36A,H36B)
3.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C30(H30A,H30B,H30C), C32(H32A,H32B,H32C), C34(H34A,H34B,
 H34C), C35(H35A,H35B,H35C), C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C39(H39A,
 H39B,H39C), C40(H40A,H40B,H40C), C41(H41A,H41B,H41C), C42(H42A,H42B,H42C)
3.d Idealised tetrahedral OH refined as rotating group:
 O4(H4), O6(H6), O16(H16)
;
_shelx_res_checksum              60646
_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 1.237
_oxdiff_exptl_absorpt_empirical_full_min 0.849