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_7156005
_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_absolute_configuration ad
_chemical_formula_moiety         'C18 H24 O7'
_chemical_formula_sum            'C18 H24 O7'
_chemical_formula_weight         352.38
_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_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                 108.591(11)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   12.308(7)
_cell_length_b                   6.220(3)
_cell_length_c                   13.145(7)
_cell_measurement_reflns_used    939
_cell_measurement_temperature    173
_cell_measurement_theta_max      67.90
_cell_measurement_theta_min      40.00
_cell_volume                     953.8(9)
_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 0.994
_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  0.0464
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9483
_diffrn_reflns_point_group_measured_fraction_full 0.886
_diffrn_reflns_point_group_measured_fraction_max 0.882
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         67.939
_diffrn_reflns_theta_min         3.548
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.791
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_correction_T_min  0.783
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             376.00
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexane/chloroform'
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.18
_refine_ls_abs_structure_details
;
 Flack x determined using 1077 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3075
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0332
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0580P)^2^+0.0507P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.0881
_reflns_Friedel_coverage         0.621
_reflns_Friedel_fraction_full    0.754
_reflns_Friedel_fraction_max     0.750
_reflns_number_gt                2897
_reflns_number_total             3075
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c7ob02697h5.cif
_cod_data_source_block           S-minus-9b
_cod_depositor_comments
'Adding full bibliography for 7156003--7156007.cif.'
_cod_database_code               7156005
_shelx_res_checksum              44432