Divergent total synthesis of the revised structures of marine anti-cancer meroterpenoids (+)-dysiherbols A-E.
Chong, Chuanke; Chang, Le; Grimm, Isabelle; Zhang, Qunlong; Kuang, Yang; Wang, Bingjian; Kang, Jingyi; Liu, Wenhui; Baars, Julian; Guo, Yuanqiang; Schmalz, Hans-Günther; Lu, Zhaoyong; Chemical science 14 (2023) 3302–3310; doi:10.1039/d3sc00173c

data_1568574
_publ_section_title
;
 Divergent total synthesis of the revised structures of marine anti-cancer
 meroterpenoids (+)-dysiherbols A-E.
;
_journal_issue                   12
_journal_name_full               'Chemical science'
_journal_page_first              3302
_journal_page_last               3310
_journal_paper_doi               10.1039/d3sc00173c
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C21 H28 O3'
_chemical_formula_sum            'C21 H28 O3'
_chemical_formula_weight         328.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-01-17
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2022-01-17 deposited with the CCDC.	2023-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.7850(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.35230(10)
_cell_length_b                   7.54950(10)
_cell_length_c                   16.84080(10)
_cell_measurement_reflns_used    6774
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.6010
_cell_measurement_theta_min      5.7970
_cell_volume                     1677.69(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.973
_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     -3.00  25.00   0.50    0.50    --    0.00 -80.00  39.00   56
  2  \w    -33.00  -5.00   0.50    0.50    --    0.00 -80.00  39.00   56
  3  \w     82.00 138.00   0.50    0.50    --  101.30  80.00 162.00  112
  4  \w     49.00 133.00   0.50    0.50    --  101.30 -80.00  39.00  168
  5  \w    -25.00  41.00   0.50    0.50    --    0.00  80.00 162.00  132
  6  \w    -37.00  35.00   0.50    0.50    --    0.00 -82.00-180.00  144
  7  \w      1.00  33.00   0.50    0.50    --    0.00 -82.00 -30.00   64
  8  \w    -39.00  -9.00   0.50    0.50    --    0.00 -82.00 -30.00   60
  9  \w     21.00  90.00   0.50    0.50    --  101.30 -77.00 120.00  138
 10  \w    110.00 135.00   0.50    0.50    --  101.30 -77.00 120.00   50
 11  \w    135.00 191.00   0.50    0.50    --  101.30  82.00  90.00  112
 12  \w     94.00 185.00   0.50    0.50    --  101.30  38.00-120.00  182
 13  \w     85.00 191.00   0.50    0.50    --  101.30  82.00-180.00  212
 14  \w     75.00 191.00   0.50    0.50    --  101.30  57.00 150.00  232
 15  \w     82.00 191.00   0.50    0.50    --  101.30  82.00  60.00  218
 16  \w     80.00 190.00   0.50    0.50    --  101.30  38.00 -90.00  220
 17  \w     84.00 110.00   0.50    0.50    --  101.30  82.00  90.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0463929000
_diffrn_orient_matrix_UB_12      -0.0330018000
_diffrn_orient_matrix_UB_13      -0.0769784000
_diffrn_orient_matrix_UB_21      0.0622017000
_diffrn_orient_matrix_UB_22      0.1719048000
_diffrn_orient_matrix_UB_23      0.0151994000
_diffrn_orient_matrix_UB_31      0.0872327000
_diffrn_orient_matrix_UB_32      -0.1049071000
_diffrn_orient_matrix_UB_33      0.0491075000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13374
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.833
_diffrn_reflns_theta_min         5.837
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_exptl_absorpt_coefficient_mu    0.672
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.300
_exptl_crystal_description       plate
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3407
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0404
_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^)+(0.0523P)^2^+0.6333P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1106
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3056
_reflns_number_total             3407
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc00173c2.cif
_cod_data_source_block           ky05062
_cod_depositor_comments
'Adding full bibliography for 1568571--1568575.cif.'
_cod_database_code               1568574
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.948
_shelx_estimated_absorpt_t_min   0.866
_reflns_odcompleteness_completeness 99.23
_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:
 C1(H1A), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C5(H5A,H5B), C6(H6A,H6B), C10(H10A,H10B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C8(H8A,H8B,H8C), C7(H7A,H7B,H7C), C13(H13A,H13B,H13C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3)
;
_shelx_res_checksum              42600
_shelx_hkl_checksum              39686
_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 1.415
_oxdiff_exptl_absorpt_empirical_full_min 0.765