Guanahanolide A, a Meroterpenoid with a Sesterterpene Skeleton from Coral-Derived Streptomyces sp.
Marchbank, Douglas H.; Ptycia-Lamky, Vernon C.; Decken, Andreas; Haltli, Bradley A.; Kerr, Russell G.; Organic Letters  (2020) –; doi:10.1021/acs.orglett.0c02208

data_1558817
_publ_section_title
;
 Guanahanolide A, a Meroterpenoid with a Sesterterpene Skeleton from
 Coral-Derived Streptomyces sp.
;
_journal_name_full               'Organic Letters'
_journal_paper_doi               10.1021/acs.orglett.0c02208
_journal_year                    2020
_chemical_absolute_configuration
;
absolute configuration was determined using Mosher's Ester method at O(4)
;
_chemical_formula_moiety         '[C37 H54 O5][C3 H6 O]'
_chemical_formula_sum            'C38.5 H57 O5.5'
_chemical_formula_weight         607.84
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                90
_cell_angle_beta                 93.585(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.479(2)
_cell_length_b                   10.076(2)
_cell_length_c                   34.499(7)
_cell_measurement_reflns_used    6112
_cell_measurement_temperature    233(2)
_cell_measurement_theta_max      55.805
_cell_measurement_theta_min      2.551
_cell_volume                     3635.5(12)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      233(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker AXS SMART1000/P4'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            12632
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.492
_diffrn_reflns_theta_min         1.999
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              K-760
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.9486
_exptl_absorpt_correction_T_min  0.7638
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.111
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1328
_exptl_crystal_recrystallization_method Acetone
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         7014
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0449
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0608P)^2^+0.5533P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1219
_reflns_Friedel_coverage         0.894
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                5064
_reflns_number_total             7014
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            rk191045.cif
_cod_data_source_block           rk191045
_cod_original_sg_symbol_H-M      'I 2'
_cod_original_formula_sum        'C38.50 H57 O5.50'
_cod_database_code               1558817
_shelx_estimated_absorpt_t_min   0.961
_shelx_estimated_absorpt_t_max   0.982
_shelx_res_checksum              5486
_shelx_hkl_checksum              35366
_shelx_fab_checksum              88848