Synthesis of the natural product descurainolide and cyclic peptides from lignin-derived aromatics.
Ojo, O. Stephen; Nardone, Brunello; Musolino, Stefania F.; Neal, Andrew R.; Wilson, Liam; Lebl, Tomas; Slawin, Alexandra M. Z.; Cordes, David B.; Taylor, James E.; Naismith, James H.; Smith, Andrew D.; Westwood, Nicholas J.; Organic & biomolecular chemistry 16 (2018) 266–273; doi:10.1039/c7ob02697h

data_7156006
_publ_section_title
;
 Synthesis of the natural product descurainolide and cyclic peptides from
 lignin-derived aromatics.
;
_journal_issue                   2
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              266
_journal_page_last               273
_journal_paper_doi               10.1039/c7ob02697h
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C13 H16 O5'
_chemical_formula_sum            'C13 H16 O5'
_chemical_formula_weight         252.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-09-09
_audit_creation_method           'by CrystalStructure 4.2'
_audit_update_record
;
2016-09-21 deposited with the CCDC.
2017-12-01 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 108.583(4)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   7.4671(13)
_cell_length_b                   32.535(5)
_cell_length_c                   5.2751(9)
_cell_measurement_reflns_used    1213
_cell_measurement_temperature    173
_cell_measurement_theta_max      46.70
_cell_measurement_theta_min      18.40
_cell_volume                     1214.7(4)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_molecular_graphics    'CrystalStructure 4.2'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Rigaku XtaLAB P100'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0680
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            16282
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.077
_diffrn_reflns_theta_min         2.716
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.891
_exptl_absorpt_correction_T_max  0.956
_exptl_absorpt_correction_T_min  0.843
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             536.00
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexane/ethyl acetate/acetone'
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.40
_refine_diff_density_min         -0.44
_refine_ls_extinction_coef       0.042(2)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     171
_refine_ls_number_reflns         2191
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0497
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0637P)^2^+0.2309P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1144
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2070
_reflns_number_total             2191
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c7ob02697h5.cif
_cod_data_source_block           anti-plus-minus-3
_cod_depositor_comments
'Adding full bibliography for 7156003--7156007.cif.'
_cod_database_code               7156006
_shelx_res_checksum              77530