Total synthesis based on the originally claimed structure of mucosin.
Gallantree-Smith, Harrison C; Antonsen, Simen G.; Görbitz, Carl H; Hansen, Trond V.; Nolsøe, Jens M J; Stenstrøm, Yngve H; Organic & biomolecular chemistry 14 (2016) 8433–8437; doi:10.1039/c6ob01511e

data_7155240
_publ_section_title
;
 Total synthesis based on the originally claimed structure of mucosin.
;
_journal_issue                   36
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8433
_journal_page_last               8437
_journal_paper_doi               10.1039/c6ob01511e
_journal_volume                  14
_journal_year                    2016
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C21 H26 N2 O6'
_chemical_formula_sum            'C21 H26 N2 O6'
_chemical_formula_weight         402.44
_chemical_name_systematic
(1S,6S,7S,8R)-8-Butyl-7-((3,5-dinitrobenzoyl)oxymethyl)bicyclo[4.3.0]non-3-ene
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2016-06-10 deposited with the CCDC.
2016-08-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.703(11)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.866(5)
_cell_length_b                   5.196(2)
_cell_length_c                   18.617(10)
_cell_measurement_reflns_used    2295
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      20.86
_cell_measurement_theta_min      2.28
_cell_volume                     1006.8(8)
_computing_cell_refinement       'APEX2 (Bruker, 2014)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'APEX2 (Bruker, 2014)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL2014 (Sheldrick, 2015b)'
_computing_structure_refinement  'SHELXT (Sheldrick, 2015a)'
_computing_structure_solution    'APEX2 (Bruker, 2014)'
_diffrn_ambient_temperature      110(2)
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_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type
'Bruker D8 Venture with Photon 100 CMOS detector'
_diffrn_measurement_method
'Sets of exposures each taken over 0.5\% \w rotation'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'InCoatec ImuS Microfocus'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2140
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_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5899
_diffrn_reflns_point_group_measured_fraction_full 0.990
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_diffrn_reflns_theta_max         20.864
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_exptl_absorpt_coefficient_mu    0.098
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_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
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_exptl_crystal_description       plate
_exptl_crystal_F_000             428
_exptl_crystal_recrystallization_method 'slow evaporation'
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         2089
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_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1009
_refine_ls_R_factor_gt           0.0854
_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^)+(0.0936P)^2^+2.6032P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2150
_refine_ls_wR_factor_ref         0.2246
_reflns_Friedel_coverage         0.742
_reflns_Friedel_fraction_full    0.553
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                1718
_reflns_number_total             2089
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob01511e2.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 7155240.cif.'
_cod_original_cell_volume        1006.8(9)
_cod_database_code               7155240
_shelxl_version_number           2013-2
_shelx_res_checksum              80743