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_1568571
_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         'C23 H32 O3, H O0.5'
_chemical_formula_sum            'C23 H33 O3.5'
_chemical_formula_weight         365.49
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-09-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-01-17 deposited with the CCDC.	2023-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   36.4809(3)
_cell_length_b                   14.42217(12)
_cell_length_c                   7.54283(7)
_cell_measurement_reflns_used    11500
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.7560
_cell_measurement_theta_min      6.3090
_cell_volume                     3968.54(6)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.967
_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    -66.00   3.00   0.50    0.50    --    0.00 -38.00 138.00  138
  2  \w    109.00 134.00   0.50    0.50    --  101.30  38.00 -66.00   50
  3  \w     45.00  70.00   0.50    0.50    --  101.30 -38.00 138.00   50
  4  \w    -36.00  39.00   0.50    0.50    --    0.00  82.00 -60.00  150
  5  \w     67.00 127.00   0.50    0.50    --  101.30 -38.00-180.00  120
  6  \w     18.00 128.00   0.50    0.50    --  101.30 -57.00  30.00  220
  7  \w     14.00  62.00   0.50    0.50    --  101.30 -38.00-180.00   96
  8  \w     12.00 138.00   0.50    0.50    --  101.30 -82.00 150.00  252
  9  \w     12.00 127.00   0.50    0.50    --  101.30 -38.00 -30.00  230
;
_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      -0.0287598000
_diffrn_orient_matrix_UB_12      0.0659441000
_diffrn_orient_matrix_UB_13      -0.0803332000
_diffrn_orient_matrix_UB_21      0.0307607000
_diffrn_orient_matrix_UB_22      0.0667442000
_diffrn_orient_matrix_UB_23      -0.0575318000
_diffrn_orient_matrix_UB_31      0.0030458000
_diffrn_orient_matrix_UB_32      -0.0510771000
_diffrn_orient_matrix_UB_33      -0.1787769000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            18252
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.877
_diffrn_reflns_theta_min         6.601
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_exptl_absorpt_coefficient_mu    0.636
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70502
_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    1.223
_exptl_crystal_description       block
_exptl_crystal_F_000             1592
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         4011
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0387
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0501P)^2^+1.7929P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1041
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3753
_reflns_number_total             4011
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc00173c2.cif
_cod_data_source_block           cl02036a
_cod_depositor_comments
'Adding full bibliography for 1568571--1568575.cif.'
_cod_original_formula_sum        'C23 H33 O3.50'
_cod_database_code               1568571
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 98.89
_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 Free rotating group:
 O10(H10)
2.b Ternary CH refined with riding coordinates:
 C00I(H00O), C00K(H00R)
2.c Secondary CH2 refined with riding coordinates:
 C006(H00A,H00B), C008(H00F,H00G), C00G(H00J,H00K), C00J(H00P,H00Q), C00N(H00V,
 H00W)
2.d Aromatic/amide H refined with riding coordinates:
 C00C(H00H), C00D(H00I)
2.e X=CH2 refined with riding coordinates:
 C00Q(H00Z,HA)
2.f Idealised Me refined as rotating group:
 C007(H00C,H00D,H00E), C00H(H00L,H00M,H00N), C00L(H00S,H00T,H00U), C00P(H00X,
 H00Y,H), C00R(H00,HB,HC)
2.g Idealised tetrahedral OH refined as rotating group:
 O004(H004)
;
_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 1.521
_oxdiff_exptl_absorpt_empirical_full_min 0.707