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_1568573
_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_absolute_configuration unk
_chemical_formula_moiety         'C23 H30 O2'
_chemical_formula_sum            'C23 H30 O2'
_chemical_formula_weight         338.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-07-24
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-07-25 deposited with the CCDC.	2023-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.745(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6931(4)
_cell_length_b                   25.8093(8)
_cell_length_c                   7.4931(3)
_cell_measurement_reflns_used    6085
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      33.5370
_cell_measurement_theta_min      2.2780
_cell_volume                     1828.38(12)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.923
_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   -120.00  60.00   1.00    1.00    --  -30.00  45.00   0.00  180
  2  \w   -120.00  30.00   1.00    1.00    --  -30.00  45.00  90.00  150
  3  \w   -120.00   0.00   1.00    1.00    --  -30.00  45.00 180.00  120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku mm007 Saturn70'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0174158000
_diffrn_orient_matrix_UB_12      0.0248140000
_diffrn_orient_matrix_UB_13      -0.0393059000
_diffrn_orient_matrix_UB_21      -0.0459883000
_diffrn_orient_matrix_UB_22      -0.0116573000
_diffrn_orient_matrix_UB_23      -0.0761551000
_diffrn_orient_matrix_UB_31      -0.0566707000
_diffrn_orient_matrix_UB_32      0.0018658000
_diffrn_orient_matrix_UB_33      0.0455438000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0531
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11231
_diffrn_reflns_point_group_measured_fraction_full 0.821
_diffrn_reflns_point_group_measured_fraction_max 0.701
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.631
_diffrn_reflns_theta_min         2.294
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 1208 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.9(9)
_refine_ls_extinction_coef       0.0050(11)
_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   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         5088
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0503
_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^)+(0.0586P)^2^+0.2589P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1148
_refine_ls_wR_factor_ref         0.1241
_reflns_Friedel_coverage         0.513
_reflns_Friedel_fraction_full    0.642
_reflns_Friedel_fraction_max     0.477
_reflns_number_gt                4333
_reflns_number_total             5088
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc00173c2.cif
_cod_data_source_block           r20220716d
_cod_depositor_comments
'Adding full bibliography for 1568571--1568575.cif.'
_cod_database_code               1568573
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.981
_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:
 C00H(H00J)
2.b Secondary CH2 refined with riding coordinates:
 C008(H00A,H00B), C00A(H00C,H00D), C00I(H00K,H00L), C00J(H00M,H00N)
2.c Aromatic/amide H refined with riding coordinates:
 C00B(H00E), C00F(H00I), C00K(H00O)
2.d Idealised Me refined as rotating group:
 C00E(H00F,H00G,H00H), C00L(H00P,H00Q,H00R), C00M(H00S,H00T,H00U), C00N(H00V,
 H00W,H00X), C00O(H00Y,H,HA), C00P(H00Z,HB,HC)
;
_shelx_res_checksum              14098
_shelx_hkl_checksum              68854
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.938
_oxdiff_exptl_absorpt_empirical_full_min 0.542