First total synthesis of type II abyssomicins: (±)-abyssomicin 2 and (±)-neoabyssomicin B.
Canko, Aleksander; Athanassopoulou, Georgia D.; Psycharis, Vassilis; Raptopoulou, Catherine P.; Herniman, Julie M.; Mouchtouris, Vasileios; Foscolos, Angeliki Sofia; Couladouros, Elias A.; Vidali, Veroniki P.; Organic & biomolecular chemistry 21 (2023) 3761–3765; doi:10.1039/d3ob00476g

data_7159302
_publ_section_title
;
 First total synthesis of type II abyssomicins: (&#xb1;)-abyssomicin 2 and
 (&#xb1;)-neoabyssomicin B.
;
_journal_issue                   18
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3761
_journal_page_last               3765
_journal_paper_doi               10.1039/d3ob00476g
_journal_volume                  21
_journal_year                    2023
_chemical_formula_sum            'C20 H24 O5'
_chemical_formula_weight         344.39
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2023-03-20 deposited with the CCDC.	2023-04-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.1705(9)
_cell_length_b                   16.4186(10)
_cell_length_c                   17.4433(10)
_cell_measurement_reflns_used    11842
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      3.13
_cell_volume                     3485.6(4)
_computing_cell_refinement       'CrystalClear, Rigaku MSC, 2005'
_computing_data_collection       'CrystalClear, Rigaku MSC, 2005'
_computing_data_reduction        'CrystalClear, Rigaku MSC, 2005'
_computing_molecular_graphics    'Diamond ver.3.2'
_computing_publication_material  'publCIF J.Appl.Cryst. 2010, 43, 920'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      160(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'RIGAKU R-AXIS SPIDER IPDS'
_diffrn_measurement_method       '\q scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0897
_diffrn_reflns_av_unetI/netI     0.0599
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18828
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_min         3.130
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6986
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'CrystalClear, Rigaku MSC, 2005'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.912
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         3801
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.912
_refine_ls_R_factor_all          0.0941
_refine_ls_R_factor_gt           0.0528
_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^)+(0.0898P)^2^+1.6671P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1308
_refine_ls_wR_factor_ref         0.1577
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2466
_reflns_number_total             3801
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00476g2.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 7159302.cif.'
_cod_database_code               7159302
_shelxl_version_number           2014/6
_shelx_res_checksum              71787